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Wireless Internet
Swimming pool
Private pool
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Private indoor pool
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Private tennis court
Cot available
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Private outdoor pool (unheated)
Private outdoor pool (heated)
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Staffed property
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Linen provided
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Private fishing lake or river
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
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Non-Smoking property
Smoking - Ask
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Beach or lakeside relaxation
Skiing – property near ski resort
Walking trips
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Golf course on site or within 15 min walk
Golf within 30mins drive
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224 Houses

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Luxury Resort Sleeps 26!

Palma Sola house

8 bedrooms
5 bathrooms

sleeps 26

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$2,289

Great rentals within 20 miles that match your search

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$271

Beach front condo in Longboat Key

Longboat Key condo

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$430

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

1 bedroom
1 bathroom

sleeps 4

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$482

Midnight Cove #532 in Siesta Key, FL- Sun, Sand & Save 7.5% to 22.5% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

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Price per night from

$144

Midnight Cove #714 in Siesta Key, FL- Sun, Sand & Save 7.5% to 22.5% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$144

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & Save 10% to 25% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$284

Shorewalk waterfront Condo Bradenton

Bradenton condo

2 bedrooms
2 bathrooms

sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

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Price per night from

$95

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$337

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

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Price per night from

$234

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

2 bedrooms
2 bathrooms

sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

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$209

Beachfront Condo Siesta Key

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

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$453

Ultimate St Pete Beach Front Rental Condo #101

St. Pete Beach apartment

2 bedrooms
2 bathrooms

sleeps 6

“Comfort and Convenience” We only stayed for 2 nights, but would not hesitate to rent here again. The location on St. Pete Beach was perfect. Even though there was temporary beach dredging going on in front of the condo this did not ruin our stay. The access to the beach was very convenient and there were less people and more room at this end, away from the larger hotels. The accomodations were just as pictured. Beautifully updated - everything clean as could be. All the conveniences were there and in working order. We look forward to the next time we can book a visit.

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$401

Condo on the Key

St. Petersburg apartment

2 bedrooms
2 bathrooms

sleeps 3

“Immaculate” I had a wonderful stay at the condo in the key. Robin was easy to work with and always responsive. The condo was very clean and well stocked. If you are looking for a place where you can lay back and relax this is a nice condo. I loved that it's in a gated area.

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$206

Amazing views, 11th flr, On the beach

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$409

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

4 bedrooms
4 bathrooms

sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

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$514

A Paradise for Golfers and Tennis players

Bradenton apartment

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 27 minutes

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Price per night from

$139

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

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$189

BEACH RESIDENCES on Siesta, aka The Hyatt – 3 Bed/3 Bath Luxury Penthouse

Siesta Key hotel apartment

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$515

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$114

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$117

Banana Cabana: By Beachside Management

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$240

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$274

Gulf Holiday: By Beachside Management

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$171

Jamaica Royale - Beachfront Tower: By Beachside Management

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$377

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$343

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$436

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key apartment

1 bedroom
1 bathroom

sleeps 3

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$194

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

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Price per night from

$115