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$108

2 BR / 1 BA / Sleeps 6

Stay on Siesta, Peppertree Bay II with Gulf View - Siesta Key vacation rentals
1 / 24

$108

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Stay on Siesta, Peppertree Bay II with Gulf View

Siesta Key house
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Completely Updated Luxurious gulf view condo located directly on Crescent Beach on Siesta Key. Peppertree Bay is a member only complex with two private pools, tennis courts, sauna, two clubhouses and an expansive fishing pier on ICW. This Gulf to Bay property is absolutely fabulous! The condo offers wonderful …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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$175

2 BR / 2 BA / Sleeps 4

1 Reviews

$175

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Right on the Beach with Extraordinary Views!

Siesta Key condo
2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Fabulous 2nd floor gulf front condo overlooking the beautiful Gulf of Mexico! Located in the desirable Island Reef complex on Siesta Key, this spacious condo features extraordinary views of the beach and sunsets from the front room, the lanai, and the master bedroom. Beautifully furnished with comfortable seating …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great Location

Left on Jun 07, 2014 for a stay in November 2013

We stayed here for the month of November last year. Very comfortable and peaceful, set in a nice complex right on the beech. Being very picky one could say that it was a little on the remote side, being about 3 miles from Siesta Key village, having said that it didn't in the least spoil our stay.

The apartment is very large and comfortable but could do with a little updating, especially the …

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$250

2 BR / 2 BA / Sleeps 8

Sophie's Cottage - Siesta Key vacation rentals
1 / 28

$250

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Sophie's Cottage

Siesta Key house
2 BR / 2 BA / Sleeps 8 | Quick view

Details

Sophie's Cottage SOPHIE'S COTTAGE: Sophie’s Cottage is a smart, sophisticated upscale waterfront retreat with a private heated pool with sunshelf, boat dock, and a short walk to Siesta Key Beach. Ideally, it accommodates 6 but can easily sleep up to 8 with 2 private bedrooms, and 2 bathrooms and 2 sleeping areas in …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$400

4 BR / 4 BA / Sleeps 8

2 Reviews

$400

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Villa Champagne

Siesta Key house
4 BR / 4 BA / Sleeps 8 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

Villa Champagne VILLA CHAMPAGNE: Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beautiful villa and gaze across the expansive living area, then further …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(2)

Great location and spacious place

Left on Oct 21, 2014 for a stay in October 2014

There were 6 adults and 4 children (ages 3-6) that stayed here and we had more than enough room with the great layout of the house. The location was great (Avineda Del Mare is just off Beach Road, just down from the public parking lot) but was "too far" to walk to Siesta for the children, so we drove. However, for adults or teens, it would have been do-able (approx. 3-4 blocks).

The supply…

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$117

3 BR / 2 BA / Sleeps 6

4 Reviews

$117

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Cortez Cottage: minutes walk to Siesta Beach

Siesta Key cottage
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Cortez Cottage is located within five minutes easy walk of Siesta Key beach, always rated in the top beaches in USA and world, powdery white sand and gorgeous Gulf of Mexico gentle waves and stunning sunsets. The cottage is just a couple of minutes walk from the heart of Siesta Village, with shops a wide variety of …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(4)

una casa muy acogedora

Left on Aug 07, 2012 for a stay in July 2012

Nos sentimos muy comodos en la casa, la disfrutamos por 2 semanas en julio y la pasamos super !!!

Tanto que pensamos volver el proximo año.

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$300

4 BR / 4 BA / Sleeps 12

1 Reviews

$300

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Villa Dom Brisa

Siesta Key house
4 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Villa Dom Brisa Villa Dom Brisa or "Sun Breeze" at 1123-1125 Crescent Street is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to our boutique collection of fine vacation homes at The Cottages. This home is part of the Las Brisa complex of two beautiful 4-BR homes offering unique sleeping…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(1)

Family Spring Break

Left on Apr 08, 2015 for a stay in April 2015

We rented both units of Villa Dom Brisa (Starfish and Coral Reef) in April of 2015 for a family vacation. The units were well decorated and very clean. Parking was more than adequate for 4 vehicles. The kitchens were properly equipped with plenty of cookware, plates, glasses, etc., for our large group. Both units included quality WiFi access, so staying up to date on work emails is not a …

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$149

2 BR / 2 BA / Sleeps 5

20 Reviews

$149

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2BR2BA 4th Floor Gulf View Siesta Key Free WiFi

Siesta Key condo
2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 20 Reviews

Details

Reviews

(20)

Last Minute Discount available for: April 26 - May 2 (6 nights)... Lots of great Summer Holiday dates available from July 5th onwards !! Jan 16-30, 2016 OPEN for next year !! We just purchased another 2BR on the beach/Gulf side of Siesta Key. Contact me for a quote and pictures... Last Minute 40% OFF Discount for …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Wireless Internet
  • Suitable for children
  • Suitable for the elderly - elevator access

Details

Reviews

(20)

summer 09 vacation

Left on Aug 06, 2010 for a stay in July 2009

we really enjoyed our stay at this excelcior condo, beaufitul with everything you need, clean, nice side view, wonderful ammenities such as the pool,location, parking, etc. would stay here again.

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$130

2 BR / 2 BA / Sleeps 4

1 / 31

$130

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Siesta Harbour 55+ Condo with a View of Intracoast

Siesta Key condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Condo has been remodelled with newly painted rooms, new flooring throughout. New king size tempurpedic bed in the master bedroom with duvet cover for your comfort with 3 pce bathroom. 2nd bedroom has 2 new single beds and can be combined together to make a king size bed. Again with soft duvet cover. Full 4 pce …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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$215

3 BR / 3 BA / Sleeps 8

28 Reviews

$215

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Seaside Villas - Deluxe Townhouse in Siesta Key

Siesta Key villa
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 28 Reviews

Details

Reviews

(28)

This deluxe townhome is ideally located in the heart of Siesta Village on Siesta Key off Sarasota Florida, just a few steps to all the shops and restaurants and only 1 1/2 blocks (it takes us three minutes to walk) to the world famous Siesta Key Crescent Beach! Relax by your private pool. This Siesta Key townhouse is …
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(28)

Great location

Left on Feb 04, 2011 for a stay in January 2011

Villa is just as pictured, very spacious. You couldn't ask for more central location to beach and restaurants. Pool was heated to 86 and very comfortable

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$400

3 BR / 3 BA / Sleeps 6

3 Reviews

$400

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3 Br, 2.5 Ba Condo Steps From Award-Winning Beach!

Siesta Key condo
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Newer complex with a total of 38 units (two buildings) built in 2003 -Marina Del Sol- offering spacious 2,500 sq ft.- 3 bedroom, 2.5 bathroom luxury condo on the 2nd floor, elevator opening to your private foyer. Large kitchen w/ granite counters, marble master bath, master closet the size of a small bedroom. Pool and…
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(3)

Fabulous, spacious condo/waterway views/walk to pristine beach

Left on Jun 30, 2011 for a stay in November 2010

My husband and four children (ages 17,15,12 & 9) all stayed in this incredibly spacious, well appointed, and gorgeous condo last November. We had a fabulous time! The layout with large LV/DN space, plus family room, plus a huge screened in balcony that overlooks and pool and Intracoastal Waterway, allows plenty of opportunity for gathering together and enough spaces for smaller groups to be in …

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$314

4 BR / 4 BA / Sleeps 12

5 Reviews

$314

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Siesta Key Deluxe Townhouse & Garden Apt (4 BR's)

Siesta Key villa
4 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

These Siesta Key deluxe townhouse rentals are located in the heart of Siesta Village - just a few steps to all the shops and restaurants and only 1 1/2 blocks (it takes us three minutes to walk) to the world famous Siesta Key Crescent Beach! Relax by your private pool. These Siesta Key townhouses are equipped with …
  • Waterfront
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(5)

Good time

Left on Apr 10, 2014 for a stay in November 2013

My wife and I stayed in the Garden apartment in November 2013. It was a very good time. It is very clean like all of the Sunnyside Properties. It is a small unit that is just fine for a couple. It is right by the pool. It is very close to the Village and Beach, so all of the fun is very accessible. The grocery store is just a couple blocks away.

I would recommend this place to anyone interested …

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$400

5 BR / 5 BA / Sleeps 14

1 / 24

$400

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Island Sol

Siesta Key house
5 BR / 5 BA / Sleeps 14 | Quick view

Details

Island Sol ISLAND SOL: Welcome to Island Sol, our exclusive 5+ bedroom, 4.5 bath home with approximately 4,000SF of air conditioned space in Siesta Key. Across the open entry and living room, you look out beyond the exterior lanai into the private courtyard which features an enclosed heated swimming pool surrounded by…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$200

4 BR / 4 BA / Sleeps 10

2 Reviews

$200

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Siesta Key Vacation Rental with Dock and Beach Access

Siesta Key house
4 BR / 4 BA / Sleeps 10 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

***NEW PROPERTY*** This luxury Siesta Key vacation rental gives easy access to both Siesta Key Beach and a day dock for your boating and fishing needs. With four bedrooms, three full bathrooms, and two half baths this property has plenty of room for up to 10 guests. Its private pool area and out door kitchenette is …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Absolutely wonderful home and location

Left on Aug 18, 2014 for a stay in August 2014

This home was breathtaking. We are a very big family with kids and adults. The house was immaculate and cleaned to perfection. We would recommended this home to any & everybody. We were beyond satisfied with the stay here ! My family and I are very picky and we couldn't say one bad thing about the house. It was quiet and the pool was so nice to have. The space in the house was more than adequate …

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$150

2 BR / 2 BA / Sleeps 6

1 / 23

$150

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Sea Wave Casita - 1119

Siesta Key house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sea Wave Casita - 1119 The Sea Wave and Sea Shell are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. (Please note: These units can be rented separately. If one unit is not available, please inquire about the availability of the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$300

4 BR / 3 BA / Sleeps 9

1 / 24

$300

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Casa De Suenos

Siesta Key house
4 BR / 3 BA / Sleeps 9 | Quick view

Details

Casa De Suenos Welcome to “Casa De Suenos”, one of the most fabulous vacation homes in Siesta Key. Newly constructed in 2013! The magic begins as you enter the foyer of this beautiful casa and gaze across the expansive living area, and deck area. You know already you made the right choice for your family and …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$214

3 BR / 3 BA / Sleeps 8

21 Reviews

$214

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Upcale Townhouse -Pool- Crescent Beach -Siesta Key

Siesta Key villa
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 21 Reviews

Details

Reviews

(21)

BEACHWALK; Three bedrooms, two and a half baths, garage, private pool, private elevator, en suite Jacuzzi tub, beach view, sleeps up to eight, steps to world famous Siesta Key - Crescent Beach... and so much more... We have two units (Unit A & Unit B) at Beachwalk - ideal for larger groups, family reunions, etc. It’…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(21)

Location, Location, Location

Left on Feb 08, 2011 for a stay in April 2010

1 block from the finest sand we've ever seen. There was my wife and myself, my son, his wife and 2 year old g'son. It was great to have the 3rd BR for the little one. We walked to the beach and dug in the sand daily. We shelled and went in the water as the weather was great. In the evenings, when we went out for dinner, the downtown was within walking distance where we found great dining both …

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$250

4 BR / 3 BA / Sleeps 8

1 Reviews

$250

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Well appointed canal front home

Siesta Key house
4 BR / 3 BA / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

This luxury Siesta Key vacation rental was built on the Grand Canal in 2005 and offers 3 bedrooms plus bonus room with 3 full baths. Its great location gives it access to Siesta key beach and Siesta Key village yet secluded enough for you to relax and enjoy the peace and quiet; no thru traffic here. Its well appointed…
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great House and Location

Left on Jul 25, 2012 for a stay in May 2012

Rent Siesta Key was great to work with. The home was gorgeouse,the location to the beach and village were perfect. The hot tub jets didn't have the thrust I would prefer. We would definitly rent the house again and from Rent Siesta Key.

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$400

4 BR / 2 BA / Sleeps 12

1 / 24

$400

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Villa Mantequilla

Siesta Key house
4 BR / 2 BA / Sleeps 12 | Quick view

Details

Villa Mantequilla VILLA MANTEQUILLA: Welcome to Villa Mantequilla, a lovely butter colored 4 bedroom, 2 bath heated pool cottage just 1 block from the Village and 3 blocks to the beach. This remarkable 4 bedroom home features a beautiful pool that overlooks the canal & a private fishing dock. You’ll love the sense …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$400

4 BR / 2 BA / Sleeps 12

1 / 25

$400

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La Casa Verde

Siesta Key house
4 BR / 2 BA / Sleeps 12 | Quick view

Details

La Casa Verde LA CASA VERDE: The waterfront cottage, 'La Casa Verde' is a very luxurious and large four [4] bedroom canal front heated pool home with two very large bathrooms in approximately 2,800SF of air conditioned living space. As you approach the home you are immediately drawn into it by volumes of lush, lavish …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$150

2 BR / 2 BA / Sleeps 6

1 / 29

$150

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Casita Sonrisa - 1117

Siesta Key house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Casita Sonrisa - 1117 Welcome to Casita Sonrisa of Villa Fiesta! Enjoy an master bedroom featuring a colorful king size bed (sleeps 2) and en suite master bathroom, and a second bedroom with two twin beds (sleeps 2) and a separate living room with a very comfy, queen size sofa sleeper (sleeps 2) all of which …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$197

4 BR / 3 BA / Sleeps 8

1 / 20

$197

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4 bedroom Key West style pool home minutes to village and beach

Siesta Key house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Stay at this large Key West style Siesta Key vacation rental home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool and Jacuzzi hot tub. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings …
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

2 BR / 2 BA / Sleeps 6

1 / 35

$150

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Coral Reef Casita - 1123

Siesta Key house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Coral Reef Casita - 1123 The Coral Reef and Star Fish Casitas are two separate units which can be uniquely configured to create Villa Brisa Marina, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross]. The décor is …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$200

2 BR / 2 BA / Sleeps 6

1 / 24

$200

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Orchid Villa - 1127

Siesta Key house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Orchid Villa - 1127 The Orchid and Hibiscus Villas are two separate units which can be uniquely configured to create “Villa Cascada," an absolutely beautiful and stunning private pool home. (Please note: These units can be rented separately. If one unit is not available, please inquire about the availability of the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$150

2 BR / 2 BA / Sleeps 6

1 Reviews

$150

Inquire

Casita Salado -1109

Siesta Key house
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Casita Salado -1109 Welcome to Casita Salado of Villa Margarita! Enjoy an master bedroom featuring a colorful king size bed (sleeps 2) and en suite master bathroom, and a second bedroom with two twin beds (sleeps 2) and a separate living room with a very comfy, queen size sofa sleeper (sleeps 2) all of which …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(1)

Fantastic Vacation at Siesta Key

Left on Jul 16, 2014 for a stay in July 2014

My wife and I with our two eight year old girls rented Casita Salado for ten wonderful days. The cottage was in excellent condition and was very clean. It was just a short couple of blocks to the beach. The beach cart and beach chairs were a great addition. All looked like brand new. Thank you for making our vacation fantastic.

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$500

4 BR / 3 BA / Sleeps 10

1 / 35

$500

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The Grand Canal Cottage

Siesta Key house
4 BR / 3 BA / Sleeps 10 | Quick view

Details

The Grand Canal Cottage THE GRAND CANAL COTTAGE: The Grand Canal Cottage, perhaps one of Siesta Key’s favorite luxury vacation homes, is a highly landscaped canal-front private luxury home featuring a heated pool with sun shelf and a separate 8-person spa. It is situated on Siesta Key within two walking blocks of …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$300

4 BR / 4 BA / Sleeps 12

1 Reviews

$300

Inquire

Villa Margarita

Siesta Key house
4 BR / 4 BA / Sleeps 12 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Villa Margarita Villa Margarita located at 1109-1111 Crescent Street is a vibrant, festive newly decorated four bedroom/four bathroom/two kitchen home now available for vacation rentals with The Cottages. It’s the latest standout in our boutique collection of fine vacation homes now available for larger groups or …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(1)

great villa with pool!

Left on Jul 16, 2014 for a stay in July 2014

We really loved this adorable unit. All furnishings seem new. Great location and the best part was the private pool shared with one other unit.

Only negative is no dishwasher in kitchen.

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$450

5 BR / 3 BA / Sleeps 14

1 / 26

$450

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Pura Vida Oasis

Siesta Key house
5 BR / 3 BA / Sleeps 14 | Quick view

Details

Pura Vida Oasis PURA VIDA OASIS: This spectacular bright cheerful, canal front cottage with a heated pool & spa has 5 bedrooms and 3 baths and it can sleep a total of 13. As you enter Pura Vida Oasis, you will notice an eclectic wine storage rack and desk area awaiting on your right and a lovely dining area with …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$295

1 BR / 1 BA / Sleeps 3

1 Reviews

$295

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Beach View / Beach Tree Suite

Siesta Key condo
1 BR / 1 BA / Sleeps 3 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Enjoy the beach view from the Beach Tree or Beach View Suite located in beautiful Siesta Key Village in Sarasota, Florida. Lounge in a hammock under sweeping coconut trees and listen to the peaceful sounds of the ocean, the Gulf of Mexico and dream away looking into the blue Florida sky. The vacation accommodations …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

This place was absolutely blissful, marvelous and hospitable.

Left on Jun 14, 2012 for a stay in May 2012

Take lots and lots of water and apply sunblock very often

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$300

4 BR / 4 BA / Sleeps 12

1 / 43

$300

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Villa Brisa Marina

Siesta Key house
4 BR / 4 BA / Sleeps 12 | Quick view

Details

Villa Brisa Marina Villa Brisa Marina or "Sea Breeze" at 1119-1121 Crescent Street is an exciting new 4BR/4BA/2Kit home just added to our boutique collection of fine vacation homes and it's sure to be a standout. This home features a brand new heated pool and a three minute walk to the Nation’s finest beach [no …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$210

2 BR / 2 BA / Sleeps 6

36 Reviews

$210

Inquire

GULF FRONT ON #1 Beach! Siesta Dunes - Pool, WiFi

Siesta Key condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 36 Reviews

Details

Reviews

(36)

Find your vacation getaway on the island paradise of Siesta Key, Florida! SIESTA KEY BEACH HAS BEEN RATED THE #1 BEACH IN AMERICA BOTH BY TRIP ADVISOR (2015) AND DR. BEACH in 2011. Our condo is located on this beautiful beach, known as "The World's Finest, Whitest Sand". A tropical vacation paradise, we …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(36)

The best vacation we have had in years!

Left on Aug 08, 2010 for a stay in July 2010

I traveled with my husband, two children and my parents. We had reservations in PCB, Fl. and ended up canceling in time because of the oil showing up on the beaches... Searched all over the net for just the right vacation spot, boy did we find it in Siesta Key, Fl. at Seista Dunes. This condo exceeded my expectations... One of my concerns was that there was no W/D in the unit, and believe me …

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$400

5 BR / 4 BA / Sleeps 12

1 / 24

$400

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The Topping Cottage

Siesta Key house
5 BR / 4 BA / Sleeps 12 | Quick view

Details

The Topping Cottage THE TOPPING COTTAGE: The Topping Cottage is a very luxurious and large five [5] bedroom, three and one-half [3.5] bath home with approximately 3,000SF of air conditioned space in Siesta Key. As you enter the foyer, you immediately notice the huge, spacious, bright living room with voluminous, high …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$270

2 BR / 2 BA / Sleeps 6

15 Reviews

$270

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Palm Bay Club Private Beach 3 min. - Pool, jacuzi

Siesta Key condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

Our condo is on the second floor and is only 3 doors from the lovely pool, jacuzzi and fishing pier. The private Cresant Beach which is deeded just for the Palm Bay Guests and is just across the street from the Bay side. It is raked every a.m. and loung chairs set out and also has a charcole grill and Pavilion to …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(15)

We loved it.

Left on Dec 28, 2011 for a stay in January 2011

We had a great visit here, the condo was exactly what we were looking for, plenty of room, nice amenities, great location. We love the area, Siesta Key is beautiful and the beach is as nice as any we've seen. We've already booked next years' stay. Thanks Nancy.

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$98

2 BR / 1 BA / Sleeps 6

1 / 18

$98

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Stay on Siesta, Island Reef, Panoramic Gulf Views

Siesta Key condo
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Island Reef is a magnificent condo facility located towards the southern end of Siesta Key. This top floor unit offers captivating views of the Gulf of Mexico, nearly 1450sqFt of living space, two bedrooms and two bathrooms. The master bedroom has a king size bed, access to the balcony, and great beach and water …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - elevator access

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$300

4 BR / 4 BA / Sleeps 12

1 / 48

$300

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Villa Fiesta

Siesta Key house
4 BR / 4 BA / Sleeps 12 | Quick view

Details

Villa Fiesta Villa Fiesta at 1115 Crescent Street is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to The Cottages collection of fine vacation homes. Villa Fiesta and its sister home, Villa Margarita are two beautiful 4-BR pool homes offering unique sleeping combinations to larger groups…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$320

3 BR / 3 BA / Sleeps 8

2 Reviews

$320

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Siesta Sandcastle 353 Calle Miramar 941.349.5500

Siesta Key villa
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Weekly Rental on Siesta Key, 600 Feet from the #1 rated Beach in the USA and the Village shops and Restaurants. Just park your car because everything is an easy walk from this property. Live entertainment abounds daily in the Village. The two units can be rented together or separate. This is perfect for groups that …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Paradise found!

Left on Apr 26, 2013 for a stay in March 2013

Stayed for 4 days with a group of friends in March (Mancation). Location is perfect for either going to the beach or partying at night in Siesta Key. Walked everywhere, no need for car. Night life is sooo fun. My friends and I golfed every day and there are countless courses to choose from. The condo has a private pool and lots of room. Cleanliness is very important for me and this unit was…

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$500

5 BR / 4 BA / Sleeps 10

2 Reviews

$500

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5 Bedroom New Penthouse-2011 Best Beach in USA

Siesta Key villa
5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Brand New 2009 Beach Villa Penthouse. 5 Bedrooms on 2 floors plus a rooftop patio. Perfect location as 3 minutes walk to beach or 2 minutes to Siesta village - corner of Ocean Blvd and Beach Rd. Gorgeous decor inside this Italian architecture with 6 furnished balconies, semi-private pool with jacuzzi, 12 foot …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(2)

Great Location - Excellent Condo

Left on Aug 20, 2012 for a stay in July 2012

Two families stayed in Late July 2012 for one week. Two sets of husband and wife plus 4 girls ages 9-15.

The condo has two floors on the 3rd and 4th floor (which is the top floor). Above on the roof is a patio with great views and a nice grill reachable with an interior stairway. The pool in the back is reachable with a separate back stairway shared with the other tenants of the building for …

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$86

0 BR / 1 BA / Sleeps 2

8 Reviews

$86

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Our Top Location! The Siesta Key Village Studio.

Siesta Key cottage
0 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Our favorite location on Siesta Key, The Siesta Key Village Studio, an accommodating ground floor one-room efficiency apartment perfectly nestled on a quiet tropical street between the best beaches, shopping and dining on the island. Wander one block to your beach, appropriately named “Sunset Beach” by residents …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(8)

Great location fantastic owners

Left on Oct 01, 2012 for a stay in September 2012

Stayed for business/pleasure. Quaint private patio, comfortable bed, kitchenette and great location. We were 2 blocks from anything we needed including some of the most beautiful sunsets I have scene.

Dan was an absolute delight to deal with. He went above an beyond any expectations, including restaurant recommendations and being accessable at all hours.

I have gone to Siesta Key several times …

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$200

3 BR / 2 BA / Sleeps 10

1 Reviews

$200

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Stay on Siesta - Beach, Gulf, Step Out To the Sand

Siesta Key house
3 BR / 2 BA / Sleeps 10 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

3 beds on Beach Rd. with some Gulf view. This remodeled townhouse is a one of a kind property. Three bedroom with king, queen, 2double beds and living room sleeper sofa. This is a step out to the sand property just north of Siesta Key Beach. Walk to Siesta Village. Views of the Gulf from almost every room. Relax in …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Great Location and Space

Left on Apr 07, 2014 for a stay in March 2014

There were 6 of us who stayed in this house. We went for a week March 22-29, 2014. The house is perfect. There are only 2 bedrooms, but there is an office that has a pull-out couch and doors that close, so it serves as a 3rd bedroom. There were 2 full baths (plus an extra spa tub in the master bedroom) and a half bath downstairs. The house was very clean and has an open layout. The owners provide…

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$195

2 BR / 1 BA / Sleeps 5

1 / 1

$195

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Pink Mango Patio Cottage

Siesta Key cottage
2 BR / 1 BA / Sleeps 5 | Quick view

Details

Vacation in your own colorful Floridian Key West style cottage accommodation with a large private patio adjacent to beautiful Siesta Key Beach in Sarasota, Florida. Pink Mango Patio Cottage are surrounded by Bougainvilleas, Passion fruits and coconut palms, located in beautiful Key West style Siesta Key Village in …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$150

2 BR / 1 BA / Sleeps 4

8 Reviews

$150

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Siesta de Mayo Cottage Weeks available in Siesta V

Siesta Key house
2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Charming 2 unit rental unit home in the Village of Siesta, Immaculate with good bedding and furnishings, cottage charm and a hot tub. Unit 1 A 1000 sq ft king and queen bedroom, original hardwood floors, open kitchen living area, enclosed front porch, full bath,all bedrooms hav been newly painted, new flat screen TV…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(8)

Stayed in Both Units! Loved Both!

Left on Dec 03, 2010 for a stay in September 2010

The combination of the location, feel of the property, amazing Siesta Key Beach, and made this an ideal place to stay. This property is literally a two minute walk from the unique village of Siesta Key. You can walk to the grocery store, bar, restaurant, shops or the beach. This property is also well maintained, very clean, and has an extremely responsive owner. I had one minor issue while I…

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$150

2 BR / 2 BA / Sleeps 6

5 Reviews

$150

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Sensational Condo & Fantastic Resort Amenities!

Siesta Key condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

The Palm Bay Club is a perfect location for your Siesta Key vacation. Bring the family and have the time of your lives! Enjoy gorgeous Bay views from the balcony of this beautifully appointed third floor condo located in the heart of Siesta Key! Spacious living area, fully equipped kitchen, and roomy bedrooms with …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(5)

Best Vacation Ever!

Left on May 07, 2010 for a stay in April 2010

We stayed at the Palm Bay Club over spring break this year and it could not have been any nicer! Vic Harris with Home & Condo Rentals was right when she told us we would not be disappointed in this lovely condo. It had everything we needed for a week in the sun and then some! We didn't spend much time in the pools because the beach was so perfect but having the option was nice.

Can't wait to …

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$400

3 BR / 2 BA / Sleeps 4

1 Reviews

$400

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Siesta Sandals Close to Village and to the Beach!

Siesta Key house
3 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Perfect beach cottage located within walking distance to village and beach or grab a bike and ride. This is a Quaint & comfortable little beach house. Very well maintained and cared for. The location is great because it is close to everything, Grocery store, Restaurants, Bars, and shopping. It has 3 Bedroom 2 baths, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

A beautiful village cottage

Left on Sep 24, 2013 for a stay in August 2013

Arrived to coconut trees and banana plants in a pretty well established front garden with plenty of parking. In a residential street. Pretty wooden typical Floridian home. Useful instructions and local contact Number left.

Spotless inside with ice-cold A/C.Spacious and homely with beautiful wooden floors. All kitchen apparatus on hand excellent laundry room plenty of towels.

Outside a lovely …

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$83

2 BR / 2 BA / Sleeps 4

1 / 41

$83

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Gulf and Bay Club 409B 2 bedrooms, Beach Front, Heated Pool, Gym

Siesta Key condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf & Bay Club #409 is guaranteed bliss. <br/><br/>Confirmed to be the "Best Sand Beach in America" by the Travel Channel, Siesta Key's residents and renters alike know they've got a very good thing. On Florida's…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$100

1 BR / 1 BA / Sleeps 4

1 Reviews

$100

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Palm Bay Club G88 Tower Condo Rental, Siesta Key, FL

Siesta Key condo
1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Take to the water or stick to the shore - the world is your proverbial oyster while staying at Siesta Key's Palm and Bay Club G88. Enjoy great comfort and value in this gulf-view suite, with all the resort amenities you can imagine. Two pools and a fantastic hot tub, a large fitness center and lit tennis courts cater …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Recomendo a todos.

Left on Aug 25, 2014 for a stay in August 2014

Voltamos depois de 19 anos ao Palm Bay e continua o mesmo porque não pode ser melhor.

Nosso apartamento na torre era maravilhoso. Muito bem equipado, não tinha defeito. Praticamente na areia com aquela praia linda tão perto. A vista não era para apraia mas era muito bonita. O condomínio muito limpo. A academia não é boa mas nem precisa-se dela com a praia perto. Emprestam livros no …

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$100

2 BR / 2 BA / Sleeps 6

8 Reviews

$100

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Gulf and Bay Club 305C GulfView 3 pools, fitness room, spa, wifi

Siesta Key condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Roll into the lap of luxury and enjoy a unit that's still sparkling new. Siesta Key Gulf and Bay Club is known to be the finest long-stay resort in the area - and this newly renovated unit with a new air conditioning and heating system, Gulf and Bay Club 305C, trumps the competition. <br/><br/>Sleeping 6, …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Gulf and Bay Club 2011

Left on May 05, 2011 for a stay in April 2011

We have been coming to Siesta Key for many years as both renters and owners. This stay at Gulf and bay Club ranks among our best experiences. The Condo was very lovely , the grounds, pools etc exceptional and the staff a delight to interact with. The only complaint is the lack of attention to the love bug problem which seemed to catch everyone by surprise as they arrived a few weeks early.The …

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$71

2 BR / 2 BA / Sleeps 6

1 / 47

$71

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Gulf and Bay Club 502D Beach Front, 3 Heated Pools, Gym, Beach

Siesta Key condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Gulf and Bay 502D will perfectly suit six nice people who deserve a month of total reward and relaxation on Crescent Beach. The resort club is unrivalled for repeat guest satisfaction and its location is smack in the middle of what the Travel Channel insists is the best sand beach in America. If you and your family …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$350

2 BR / 2 BA / Sleeps 6

1 / 21

$350

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Siesta Dunes 201, 2nd Floor, Spa, Beach, Large Heated Pool, Wifi

Siesta Key condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it's easy on the wallet while its lovely atmosphere makes it a great home to return to for relaxing …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$83

2 BR / 2 BA / Sleeps 6

9 Reviews

$83

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Gulf and Bay Club 204C, Beach Front, 3 pools, spa, wifi

Siesta Key condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf & Bay Club 204C, you'll enjoy luxury and comfort in more than 1,500 sq ft of beachfront property, including a lovely lanai. And use of resort amenities is included! 28 day minimum stay.<br/><br/>Gulf & Bay Club 204C is …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(9)

Left on Dec 06, 2010 for a stay in November 2010

We really enjoyed our stay. The condo was very comfortable and well equipped. Looking forward to a return trip to this property.

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$79

2 BR / 2 BA / Sleeps 6

2 Reviews

$79

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Excelsior 107, 1st Floor, 2 heated pool, spa, wifi, beach access

Siesta Key condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

With the Bay in back and the Gulf in front, our condo at Excelsior 107 sits on a little strip of paradise! Located in a luxurious resort with everything from heated pools and outdoor grills to private beach access, it's a tropical getaway on one of the world's finest beaches.<br/><br/>Just yards from the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great place to stay!

Left on Jun 20, 2011 for a stay in June 2011

We had a great time and were glad we decided to stay 2 weeks.

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$100

2 BR / 2 BA / Sleeps 6

37 Reviews

$100

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Siesta Dunes 104, Siesta Key Gulf, Spa, Heated Pool, Wifi

Siesta Key condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 37 Reviews

Details

Reviews

(37)

Decked in pure tropical style, Siesta Dunes Beach 104 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it's easy on the wallet while its lovely atmosphere makes it a great home to return to for relaxing …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(37)

Left on Jul 08, 2008 for a stay in June 2008

Christina and Dennis were extremely helpful when we arrived in Sarasota. We had originally signed up to rent a condo at Jamica Royale. When we arrived, we felt it was not what we had envisioned. I called Christina, and within 1/2 hour, Christina was at our doorstep, offering several other locations for the week. Thank you for all your assistance. It was a pleasure! Jody Baker

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