Showing

PreviousNext property

$643

4 BR / 3 BA / Sleeps 8

1 Reviews

$643

Inquire

Aguazul

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

Details

Reviews

(1)

Village Permit #VR-09-82 You can not rent this property for less than one week. Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Aguazul. Aguazul is located at Mile Marker 89, in beautiful Islamorada. This gorgeous four bedroom,three bath home will sleep 8 people very comfortably. Aguazul has everything you …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

The perfect getaway

Left on Sep 26, 2011 for a stay in August 2011

My family had a fantastic vacation. This home is located really close to some great restaurants. It was so nice to sit back and relax all day while the kids played in the ocean and pool.

PreviousNext property

$500

2 BR / 2 BA / Sleeps 6

1 Reviews

$500

Book

Islamorada Waterfront Paradise 2

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

**We do not use the optional calendar feature on this listing. ** This is a very popular rental, so book your preferred week well in advance of peak season! I reply to EVERY inquiry. If you do not receive a reply, please contact me again! Email me for additional pictures of this wonderful hideaway. EVERY RENTER IS…
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

A little paradise

Left on Feb 18, 2015 for a stay in January 2015

We had a great family time in this house.

It's perfectly located in the Keys. It's clean, well equiped, quiet and peaceful.

PreviousNext property

$100

2 BR / 2 BA / Sleeps 6

2 Reviews

$100

Inquire

Summer Sea #418 - 28 Night Minimum

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

Details

Reviews

(2)

This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset cocktail in the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Heaven in Islamorada, Florida

Left on Aug 23, 2011 for a stay in July 2011

Rented a 2/2 condo for the month of July 2011.
Great location, nice amenities,clean,wonderful view, friendly staff and condo owners.
Excellent price.
I will definitely do this again soon.

PreviousNext property

$600

4 BR / 3 BA / Sleeps 8

1 Reviews

$600

Inquire

Latitude

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

****This house cannot rent for less than 28 days, per County Ordinance**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and two guest rooms. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

A wonderful week with extended family

Left on Jun 16, 2013 for a stay in June 2013

Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching a huge variety of sealife from the dock. We saw nurse and bonnet-head sharks, crabs, puffer fish, a turtle, stingrays and much more. The house was convenient to several very good restaurants (Pierre's, Islamorada Fish …

PreviousNext property

$117

3 BR / 2 BA / Sleeps 6

258 Mohawk St - 28 Night Minimum!!!!!!! - Islamorada vacation rentals
1 / 1

$117

Inquire

258 Mohawk St - 28 Night Minimum!!!!!!!

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,500 per month. The residence …
  • Waterfront
  • Internet Access
  • A/C or climate control
  • Porch
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$175

3 BR / 3 BA / Sleeps 8

1 Reviews

$175

Inquire

BLUE WATER RETREAT

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is located on a canal …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Blue Water = Everything that you want

Left on Jul 15, 2013 for a stay in July 2013

This place delivers.

You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of all the house is on a peninsula that looks at the ocean from all sides and is just a few miles south of most of that main attractions in Islamorada giving the home a calm but close feel. Also working…

PreviousNext property

$275

3 BR / 2 BA / Sleeps 6

3 Reviews

$275

Book

Islamorada “The Getaway” Relax in Florida Keys!

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling, diving and boating…
  • Waterfront
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

The Keys at its Best

Left on Mar 26, 2014 for a stay in March 2014

We stayed at "The Getaway" for spring break...a break from it all. This is place was wonderful! First, Luis and Paula were wonderful from initial inquiries, to providing suggestions for things to do and places to go, through the end of our stay and follow up. They were available by phone and email if we had a question. The home was wonderfully decorated and clean! two sets of bunk beds and a…

PreviousNext property

$643

4 BR / 3 BA / Sleeps 8

1 / 1

$643

Inquire

50 Schooner Bay Rd - Aguazul

4 BR / 3 BA / Sleeps 8 | Quick view

Details

How about sipping coffee and watching the sun come up as you fish off the end of your very own 300 foot pier? Sounds good, right? Well, that's just one reason to stage your upcoming vacation at this lovely, hacienda-style home on a quaint and private oceanfront street in Islamorada. CLICK HERE to view photos on a …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$150

3 BR / 2 BA / Sleeps 6

1 / 1

$150

Inquire

127 Tequesta - 28 Night Minimum

3 BR / 2 BA / Sleeps 6 | Quick view

Details

N/A
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$380

3 BR / 3 BA / Sleeps 6

3 Reviews

$380

Inquire

75333 Overseas Hwy

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

Details

Reviews

(3)

Exceptional oceanfront home equipped with a sandy beach and forever views! Exquisite design and rich appointments compliment this oceanfront home in Lower Matecumbe, (mile marker 75, South Islamorada). You will enjoy private terraces from each bedroom overlooking picturesque sunrises and panoramic views of the open …
  • Internet Access
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Heaven on Earth

Left on Jan 30, 2013 for a stay in December 2012

My husband and I rented this home for the week of Christmas. We also invited our respective parents. This is the most peaceful home in Islamorada. Centrally located to the upper and lower keys.

There home is well appointed with everything you need except for the groceries and tolietries that you will need. All appliances work well and the home is in excellent condition.

Freewheeler realty…

PreviousNext property

$286

3 BR / 3 BA / Sleeps 6

4 Reviews

$286

Inquire

130 Bayview Isle Dr

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Great neighborhood located on Snake Creek. 2 bedroom/2 bath upstairs with a bunkroom and bath downstairs. An outdoor hot tub and sundeck complement the excellent deep water dockage and easy bay or ocean access. There is room for about a 36 foot boat or less. Mile Marker 86, Bayside. VACATION RENTAL LICENSE: VR-069 …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

I loved this place!

Left on Nov 02, 2010 for a stay in October 2010

Both the home and the location in Islamorada were perfect! I spent a week at 130 Bayview Isle and it was exactly what I hoped it to be. It was incredibly quiet and felt like home. If the home is for rent next year, I will absolutely rent it again. Awesome place!

PreviousNext property

$129

2 BR / 2 BA / Sleeps 4

1 Reviews

$129

Inquire

Futura Condo 205

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the community's two tennis courts…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

This condo has everything and more

Left on May 17, 2013 for a stay in March 2013

This condo was perfect for our vacation. While there was only 2 of us a family of 4 could definitely fit. The kitchen was incredibly well stocked with everything you could possibly need as well as extra towels and linens in the closet. Living room had a huge comfortable couch and TV. There was also a deck with chairs overlooking the tennis courts and pool.

The washer and dryer were outside …

PreviousNext property

$215

3 BR / 2 BA / Sleeps 6

1 Reviews

$215

Book

Islamorada bay front condo with deep water 36ft boat slip

3 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Beautiful bayside condo, 3bedrooms 2baths, sleeps 6 comfortably, new sealy beds in all rooms with cable and wifi. Newly furnished and clean. Comes with 36 foot boat slip in the marina. There is a boat ramp on the property along with a brand new pool. Deep water dockage and deep channel to bay, minutes to snake …
  • Waterfront
  • Shared outdoor pool (unheated)
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(1)

Good rental for a boater's vacation

Left on Jun 15, 2014 for a stay in June 2014

We spent a full week at this Futura Yacht Club rental, which we enjoyed very much. Here are the pro's and con's:

Pro:

Boat slip accommodated our 29 foot boat well

Fresh water wash downs at each slip

Well lit dock

BBQ facilities by dock

Tiki hut/beach chairs on community beach area with nice gulf view/sunsets!!!

Easy access to ocean via snake creek

Large clean pool with lots of seating …

PreviousNext property

$236

3 BR / 2 BA / Sleeps 6

2 Reviews

$236

Inquire

155 Azalea Street

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Plantation Key canal home. Nice new home with screened porch and pool table! Delightfully furnished for a comfortable stay. Excellent outdoor entertaining space, great for soaking in the hot tub, gazing at fish in the canal, having cocktails under the Chickee, or for the kids to run around and play. Great dockage with…
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Loved the place and location!!

Left on Aug 11, 2013 for a stay in July 2013

We completely enjoyed our stay. Plenty of room for 6 ppl to sleep. Nice sized kitchen and dining area. We stayed with two young children and they loved it. Great location for both gulf access and on land access to grocery, dining and all. We can't wait to go back.

PreviousNext property

$329

3 BR / 3 BA / Sleeps 6

6 Reviews

$329

Inquire

138 Bayview Isle

3 BR / 3 BA / Sleeps 6 | Quick view
“ Very Good ” 6 Reviews

Details

Reviews

(6)

Modern canal home with views of Snake Creek. The property is completely fenced in. Third level master suite with private master balcony. Well furnished with all the extras. Easy ocean or bay access and dockage up to 50 feet. Open floor plan with regulation pool table and screened in porch. This home's entertainment …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Perfect location

Left on May 27, 2011 for a stay in May 2011

Other then having to Clean-up the bug's it was great.

PreviousNext property

$100

2 BR / 1 BA / Sleeps 1

1 / 1

$100

Inquire

241 Tollgate Blvd - 28 NIGHT MINIMUM!!!!!!!!!!!!!!

2 BR / 1 BA / Sleeps 1 | Quick view

Details

"Cute & Keysy" perfectly describe this Conch home! Located in the Tollgate Shores subdivision of Lower Matecumbe (south Islamorada), this delightfully quaint home has lots of character, charm, and is well-maintained. You'll enjoy sea breezes and the smell of salty air coming through the windows of the sunroom, or …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$500

4 BR / 3 BA / Sleeps 8

4 Reviews

$500

Inquire

101 Palo de Oro

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Great pool home in desirable Venetian Shores. This 4 bedroom/3 bath home is roomy and has great porches overlooking the wide, clean canal. Lovely master suite on the top floor with it's own balcony. Comfortably furnished pool home with 90 feet of excellent deep water dockage on a wide canal leading directly to Snake …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Wonderful

Left on Jul 15, 2010 for a stay in June 2010

We have stayed at this house 2 years in a row. The house is comfortable and a great location. The area has wonderful restaurants and fishing is great. We plan on staying next year for 2 weeks.

PreviousNext property

$110

3 BR / 2 BA / Sleeps 8

1 / 29

$110

Book

DEC & APRIL DEAL MONTH MINIMUM ENJOY! (phone: hidden)

3 BR / 2 BA / Sleeps 8 | Quick view

Details

ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed; great pool , tennis…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$600

4 BR / 0 BA / Sleeps 8

1 Reviews

$600

Inquire

76190 Overseas Highway - Casa Dorado

4 BR / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Casa Dorado is a premier rental vacation home on Lower Matecumbe Key in Islamorada, Florida. Completely renovated in 2014, the spacious living and dining areas, four bedrooms, and three and a half bathrooms will make for a very comfortable stay during your visit to the Florida Keys. The house is located on the Florida…
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Casa Dorado delivers!

Left on Dec 26, 2014 for a stay in December 2014

The house is newly remodeled and in great condition. Very clean- which was a must for me! The views are wonderful. We thouroghly enjoyed the week we spent there (myself, my husband, our 24yr old daughter and her friend). It was a great location for biking, walking, kayaking and paddle boarding. The home has a pool, but we did not use it because it was not heated. We highly recommend Casa Dorado.

PreviousNext property

$175

4 BR / 4 BA / Sleeps 8

1 / 36

$175

Inquire

164 Plantation Shores Drive - 28 NIGHT MINIMUM

4 BR / 4 BA / Sleeps 8 | Quick view

Details

This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage. The home sits on a …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$286

3 BR / 2 BA / Sleeps 7

6 Reviews

$286

Inquire

76300 Overseas Highway

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. VACATION RENTAL LICENSE: VR-039 CLICK HERE to view photos on a mobile device. Additional amenities …
  • Waterfront
  • Internet Access
  • Porch
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Great views and convenient to the entire Keys chain

Left on Feb 09, 2011 for a stay in December 2010

Great location, fantastic views, great access to the Bay and atlantic. Older home but clean and well maintained. Nicely situated in the Keys for access to Key West to Key Largo. Home had only basic cable and the dish washer did not work but overall would recommend the home. If your looking for luxury, this is not your place but if you want to just experience the keys and all they offer it's …

PreviousNext property

$3,000

2 BR / 2 BA / Sleeps 4

3 Reviews

$3,000

Inquire

2-bed,1.5-bath Condos On The Bay, Islamorada

2 BR / 2 BA / Sleeps 4 | Quick view
“ Average ” 3 Reviews

Details

Reviews

(3)

Complex Amenities - MM 88.5 - Building has five floors - Large swimming pool & children's pool - Exercise room with sauna - Laundry room on each floor - Billiard and Ping-Pong room - Adult party lounge - Cookout facilities - Direct access to Florida Bay and then ocean - Minutes from Islamorada, “sport fishing …
  • Waterfront
  • Ocean or water views
  • Sauna
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(3)

Beautiful Vacation Spot- Great for families!

Left on Apr 18, 2013 for a stay in April 2013

The condo in Islamorada was clean, updated, and nicely furnished, perfect for our family of 4. The kitchen is updated with granite counters & stainless steel appliances. The view from the living area in the condo is simply gorgeous-crystal clear water. There is a cozy little deck for drinking coffee in the morning and watching sunsets in the evening. The master bedroom has a king size bed, …

PreviousNext property

$200

1 BR / 1 BA / Sleeps 2

3 Reviews

$200

Book

Islamorada Waterfront Paradise 1

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Dive right into paradise while staying at Casa Rio. With a beautiful view from a raised master suite in the Florida Keys you can quickly relax and transform into 'island time.' This exclusive bayside home is situated in a secluded location on Islamorada with quick access to the Florida Bay and Atlantic Ocean. Your …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control

Details

Reviews

(3)

Great vacation location

Left on Mar 03, 2014 for a stay in February 2014

We had a lovely time staying here. The highlights were the large back yard on the water with the chiki hut and the many other places to relax on the dock. And we even saw a manatee! Having the bicycles to explore the neighborhood and the double kayak to get out on the water was a bonus. The room itself was spotless and very well set up. And fishing off the dock was so much fun! Loved having the …

PreviousNext property

$167

2 BR / 2 BA / Sleeps 4

1 / 24

$167

Inquire

OCEAN HARBOUR K4

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month New on the rental market. This is your opportunity to secure your winter getaway at a luxurious oceanfront condo in one of Islamorada's most prestigious condominium communities. Ocean front dockage is available for boats up to 28' in length (separate rental); heated free-form swimming pool, …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$500

3 BR / 3 BA / Sleeps 8

22 Reviews

$500

Inquire

Venetian Tropics 3 bedroom pool home on canal or do you need 2 bedroom only?If yes check the savings.

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 22 Reviews

Details

Reviews

(22)

Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email VenetianTropics@aol.com for the application. Weekly vacation rental…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(22)

Favorite trip ever

Left on Mar 01, 2011 for a stay in April 2007

This was the best vacation we ever had, and it had much to do with this rental ! We drove from Maryland and pulled our boat. It was great being able to put it in the water and have it right behind where we stayed. The home was beautiful, clean and well equipped for vacationing !!! The kids loved the pool !!! We will Definetly be back !!!

PreviousNext property

$329

3 BR / 3 BA / Sleeps 6

6 Reviews

$329

Inquire

137 Leserra Lane

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

Details

Reviews

(6)

Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two flat panel TV's in …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

We had a very relaxing and fun-filled vacation

Left on Jul 15, 2010 for a stay in June 2010

The house is in a great location in Lower Matecumbe. Robbie's restaurant is only one mile away which we went to three times (twice by car, once by boat). We also went to anne's Beach twice with our dogs. The house is great for pets, the yard is fenced in and there is plenty of room for the dogs to run around.

PreviousNext property

$429

5 BR / 4 BA / Sleeps 10

8 Reviews

$429

Inquire

140 Atlantic Lane

5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Amazing ocean views can be enjoyed from this beautiful stilt home with seperate mother-in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile Marker 76.5, Oceanside. …
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Summer vacation 2010

Left on Sep 13, 2010 for a stay in August 2010

Overall nice place, kitchen items were not very organized, and place could use a deep cleaning

PreviousNext property

$77

2 BR / 2 BA / Sleeps 4

1 / 14

$77

Inquire

THE PALMS 402

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony. Watch the fishing boats …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$250

2 BR / 2 BA / Sleeps 4

1 / 20

$250

Book

Oceanfrontparadise: 209

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of divers too. Our …
  • Balcony or terrace
  • Linens Provided
  • Towels Provided
  • Freezer
  • Microwave
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$117

3 BR / 3 BA / Sleeps 6

1 / 1

$117

Inquire

157 Caloosa St - 28 Night Minimum

3 BR / 3 BA / Sleeps 6 | Quick view

Details

This is a beautifully, modern home with two separate quarters. The main living area is located on the ground level with 2 bedrooms & 1 bathroom. It is equipped with full kitchen (blender & toaster included), DirectV, wireless internet, Netflix, and washer & dryer. Click here to view this photo slideshow on a mobile …
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$215

2 BR / 2 BA / Sleeps 4

16 Reviews

$215

Inquire

132 Columbus Drive

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 16 Reviews

Details

Reviews

(16)

This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world and different keys …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(16)

Exactly what we were looking for

Left on Jul 14, 2010 for a stay in June 2010

We were looking for a waterfront rental to give us more room than a reg hotel or bungalow. We were not looking for a pool and wanted something laid back. This was exactly what we were looking for and suited us, a fmily of 4 to the proverbial T. Not for a larger group/family or for folks looking for "Island Luxe".

PreviousNext property

$929

4 BR / 4 BA / Sleeps 10

13 Reviews

$929

Inquire

75731 Overseas Highway

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 13 Reviews

Details

Reviews

(13)

Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and other shopping are plentiful in Islamorada. Pass through a private …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

Paradise!!!

Left on Jul 14, 2010 for a stay in May 2010

Michelle Sorell was a great help and everything was just perfect. I hated to leave. the property is well maintained and Randy was also nice with all our grandboys that came in to visit while we were there. Thanks again for making our vacation so wonderful.

PreviousNext property

$215

3 BR / 2 BA / Sleeps 6

15 Reviews

$215

Inquire

Windy Cove Townhome #1

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Television
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

Absolutely awesome

Left on Jun 21, 2010 for a stay in June 2010

Windy Cove was a wonderful place.
The view was amazing. The location was perfect. We will be staying here again!

PreviousNext property

$715

4 BR / 3 BA / Sleeps 10

1 / 8

$715

Inquire

82754 Overseas Highway

4 BR / 3 BA / Sleeps 10 | Quick view

Details

OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully equiped kitchen with the …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$358

4 BR / 3 BA / Sleeps 8

4 Reviews

$358

Inquire

76004 Overseas Highway

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees. Large sandy beach and great dock. Interior photos available! Mile Marker 76, Bayside. Home has 2 bedrooms & 2 bathrooms upstairs, and a separate 2 bedroom, 2 bathroom apartment …
  • A/C or climate control
  • Garage
  • Grill
  • Dishwasher
  • Microwave
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

A Week in a Tropical Paradise.

Left on Aug 03, 2010 for a stay in July 2010

We had a fantastic time. Incredible home on the water with boat dock. Plenty of room and privacy. Accommodations were five star. We highly recommend it.

PreviousNext property

$758

5 BR / 3 BA / Sleeps 10

16 Reviews

$758

Inquire

87445 Old Hwy

5 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 16 Reviews

Details

Reviews

(16)

This oceanfront home will surely get you in a Keys state of mind. Featuring five bedrooms, a pool, and an expansive private beach, its ideal for anything from a reunion of extended family or friends, to a small wedding, to a relaxing family vacation. The 4,300 square foot house will capture your attention at the …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Garage
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(16)

Great Location, house needs some nimor work

Left on Apr 07, 2011 for a stay in March 2011

Nice house, dirty carpets, screens on doors need repair, with minor cleaning and repairs this house could be great

PreviousNext property

$358

2 BR / 2 BA / Sleeps 6

1 Reviews

$358

Inquire

LITTLE BAY - Cottage

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

Details

Reviews

(1)

Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a full bath. To the right is …
  • Ocean or water views
  • Internet Access
  • Parking
  • Grill
  • Refrigerator
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

A place where memories are made.....

Left on May 28, 2013 for a stay in May 2013

The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for my 9 year old twins to go exploring on their own. It truly has something for everyone. We cooked, laid out, watched the sunset, even took a dip in the bay. It was really lovely. We will definitely be returning.

PreviousNext property

$97

2 BR / 2 BA / Sleeps 6

1 / 26

$97

Inquire

THE PALMS 405 - 93

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room furnishings and the flat screen TV, not …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$300

3 BR / 2 BA / Sleeps 6

1 Reviews

$300

Inquire

107 San Remo

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Affordable Venetian Shores canal home at the Mile Marker 86, Bay-side. Nice decor, recently updated with a private downstairs apartment. Two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs (with a complete kitchen and living room). Easy ocean or bay access via Snake Creek. CLICK HERE to view …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Experience of a lifetime!

Left on Feb 09, 2014 for a stay in November 2013

Love the location, house was extremely well equipped, comfortable, Very accommodating to a wide range of taste and activities!

PreviousNext property

$179

1 BR / 1 BA / Sleeps 2

1 / 4

$179

Book

CASA THORN

1 BR / 1 BA / Sleeps 2 | Quick view

Details

Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast. LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING YET MINUTES TO FISHING…
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Pet friendly
  • Suitable for children

PreviousNext property

$300

2 BR / 3 BA / Sleeps 5

22 Reviews

$300

Book

Luxurious Anglers Reef with Boat Slip, Pool, Ocean

2 BR / 3 BA / Sleeps 5 | Quick view
“ Excellent ” 22 Reviews

Details

Reviews

(22)

House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich hard wood floors, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(22)

Beautiful luxury and an absolute great stay in Keys! No hesitati

Left on Oct 18, 2012 for a stay in October 2012

This beautiful condo in Islamorada is pristine clean, has all the updates needed and is centrally and perfectly located if staying in the Keys! Jo (the owner) made us feel like family, gave us wonderful recommendations of who to take us snorkeling, diving, kayak rental, where to eat and even went out of her way to purchase a charcoal grill so we could cook out if we wanted to stay "home". I was …

PreviousNext property

$172

2 BR / 2 BA / Sleeps 4

3 Reviews

$172

Inquire

Sea Gulls Condo - Unit 406

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

This newly remodeled & renovated (in 2012), two bedroom, Sea Gulls Condo unit, located on the oceanside of Plantation Key at Mile Marker 90, has an awesome view! Unit is comfortably and stylishly furnished, has TVs in the living room, two queen beds and a sleeper sofa. The Sea Gulls community features a fish cleaning …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Sauna
  • Internet Access
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Adequate

Left on May 24, 2012 for a stay in April 2012

The condo provided plenty of space for two couples. The complex is quiet. The pool is nice and the meditation beach(tiny) was relaxing. The condo itself was very dated. The beds were comfortable. The living room furniture was stained. The entire condo had an odor but tolerable. Possibly it had not been used for some time, not sure. Smelled musky. The balcony is large and was enjoyable for…

PreviousNext property

$315

2 BR / 3 BA / Sleeps 4

1 / 1

$315

Inquire

Angler's Reef | 130 Anglers Way

2 BR / 3 BA / Sleeps 4 | Quick view

Details

Add some Caribbean spice to your next visit to the Florida Keys. This two-bedroom/two-and-half bath villa sits within Angler's Reef, a charming community of detached town homes that take their inspiration from the architecture of the British West Indies. Located at mile marker 85, on Windley Key, it's the perfect …
  • Ocean or water views
  • Internet Access
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$133

2 BR / 2 BA / Sleeps 4

1 / 17

$133

Inquire

BEACON REEF 222

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2 spacious bedrooms, 2 full baths…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$217

3 BR / 2 BA / Sleeps 6

1 Reviews

$217

Inquire

MY PARADISE

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the moment you arrive, you'll know …
  • Ocean or water views
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

My Paradise from architect's perspective

Left on Jan 23, 2013 for a stay in April 2012

My wife and I spend a month at My Paradise and, as an architect, there are certain aspects that bear mention. First, if the weather is mild, you can open the wall of folding glass doors and unite the main interior room (dining, den and kitchen) with the oversize teak deck. The deck itself is a marvel. A covered sitting area gets you out of the sun, with six teak sun loungers for warming up and …

PreviousNext property

$67

2 BR / 2 BA / Sleeps 6

1 / 16

$67

Inquire

BOATER'S DELIGHT

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Minimum Rental: 1 Year Beautifully furnished, this almost new single family stilt home sits on an ocean side canal front lot. Bring your boat and your swim suit! This 2 bedroom, 2 bath home has everything you need, including a laundry room with a clothes washer and dryer and a fully equipped kitchen. Enjoy your …
  • Hot Tub/Jacuzzi
  • Patio
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$358

2 BR / 2 BA / Sleeps 6

3 Reviews

$358

Inquire

LITTLE BAY - Upper Duplex

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Minimum Rental: 7 Nights Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps up to 6 people - …
  • Ocean or water views
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(3)

Iguanas, sunshine and the sea in your backyard.......

Left on Nov 05, 2012 for a stay in October 2012

We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach! The apartment couldn't have been nicer, 2 bed, 2 bath with the second bedroom having twin beds so was perfect for the children (6 & 12). The apartment was well laid out with a HUGE deck overlooking the garden (iguanas!) and …

PreviousNext property

$123

3 BR / 2 BA / Sleeps 6

1 / 21

$123

Inquire

THE PALMS 316

3 BR / 2 BA / Sleeps 6 | Quick view

Details

MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting atmosphere. You'll really…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$358

2 BR / 2 BA / Sleeps 6

4 Reviews

$358

Inquire

LITTLE BAY - Lower Duplex

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Minimum Rental: 7 Nights Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up to 6 people - rent …
  • Ocean or water views
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Paradise!

Left on Jun 03, 2013 for a stay in May 2013

My family and I spent Memorial Day Weekend at this gorgeous property and it was like paradise! Not only was it beautiful inside and out it had a sophisticated charm and inviting ora from the moment you entered the property and opened the door! This place screams class while still giving you the feeling of total relaxation. The beds are amazing!!! The grounds are clean and beautiful and we even …

PreviousNext property

$133

2 BR / 2 BA / Sleeps 4

1 / 18

$133

Inquire

BEACON REEF 211

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit provides spectacular ocean views. It is one of the few units that offer spiral stairs to the ground level directly from your private balcony. The …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 2 3
page 2 of 3
Load more