We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Villas Islamorada, FL

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 146 Rentals in Islamorada
loading...
Sort by
From
$315
Per Night
1 / 20
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
From
$608
Per Night
1 / 15
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (3) Make Enquiry
From
$1,264
Per Week
1 / 19
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (2) Make Enquiry
From
$2,187
Per Month
1 / 15
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed... View all property information
Make Enquiry
From
$1,267
Per Night
1 / 18
5 Bedrooms, 4 Bathrooms, Sleeps 16
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new kitchen... View all property information
Make Enquiry
4 of 5 stars Reviewed 7 November 2014
We had a wonderful time, wedding on the beach, beautiful view, snorkeling of the beach, lots of birds visiting. But when it rains you need your wellingtons, the drive way up to...
5 of 5 stars Reviewed 12 May 2013
We booked this fabulous ocean front home for our 20th Anniversary as we decided to bring our four teenagers with us. This was the first time we had ever rented a vacation...
See all reviews
Enquire for rates
1 / 8
Payment Protection
4 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
This large 4 bedroom house sits jst 10 feet from a 116 foot dock. You are right around the corner from 4 bridges in a row where yo can get to the Ocean or Bay within a few minutes. View all property information
Make Enquiry
5 of 5 stars Reviewed 27 August 2014
We had a great stay! Ended up renting both houses for a weekend stay. Had 15 people and 4 boats. We had a great weekend, Helen and her son Rob were very accommodating and quickly...
See all reviews
From
$334
Per Night
1 / 27
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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,... View all property information
Make Enquiry
From
$365
Per Night
1 / 35
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Gym
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This remodeled 2 bedroom 2 bath condo is directly on the Atlantic Ocean with ground access via a spiral staircase. Stunning views from the Master bedroom and balcony. Wake up to the sunrise and enjoy your leisurely day on the boat, at the nearby sand bar, or lounge in the zero entry pool. There... View all property information
Make Enquiry
5 of 5 stars Reviewed 7 January 2012
My husband and I stayed here for almost 2 weeks for our honeymoon/vacation over the Christmas holiday. We were nervous about renting something over the internet that we had never...
See all reviews
From
$1,041
Per Night
1 / 27
4 Bedrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
Make Enquiry
From
$608
Per Night
1 / 38
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (22) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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.... View all property information
Make Enquiry
5 of 5 stars Reviewed 19 May 2013
This home was the perfect location for our spring break vacation. It was so central to many activities on the keys and so many wonderful restaurants. The home is very nice, a...
5 of 5 stars Reviewed 21 January 2013
I recently returned from Islamorada where the weather was low 80s and sunny every day. JoAn and Barbara were exceedingly helpful. The house was perfect for the needs of six of...
See all reviews
Get the List
From
$778
Per Night
1 / 11
5 Bedrooms, 4 Bathrooms, Sleeps 9
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Millionaire's Row! Beautiful home with private heated swimming pool directly on the ocean in Islamorada. This home offers excellent views of the ocean from many rooms. 5 bedroom, 4 bath owners home is beautifully furnished with ocean views from patio, living room (upper and lower), and dining room... View all property information
Make Enquiry
From
$3,615
Per Week
1 / 49
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
FOR ADDITIONAL REVIEWS GO TO "HOMEAWAY.COM" LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, RENTAL PATTERN... View all property information
Make Enquiry
5 of 5 stars Reviewed 14 May 2014
We had such a wonderful time at Paradise Point!! The views were beautiful!!! The kids loved the pool and all the sealife we saw. Many fish and stingrays, just to name a few...
5 of 5 stars Reviewed 14 February 2014
My week started when my wife and I along with our two friends met Juan Sanchez at this home he calls Paradise (which it really is). The man from my first e mail to him to locking...
See all reviews
From
$468
Per Night
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA View Map Accommodations: House, 3 Bedrooms, 2 Baths, sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three... View all property information
Make Enquiry
5 of 5 stars Reviewed 12 May 2014
We loved staying at Villa Marlin, and the owner was very helpful before and during our stay. The home is prettier than the pictures, and we felt right at home!
See all reviews
From
$191
Per Night
1 / 25
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Private Beach
  • Satellite TV
  • Shared Outdoor Pool...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, basketball and... View all property information
Make Enquiry
3 of 5 stars Reviewed 5 March 2014
This was a nice rental. There seems to have been a nice soft update done not to long ago, and it appeared that some features were still being upgraded. The building is clean...
5 of 5 stars Reviewed 14 January 2012
The condo was great! It was clean and located in a great place in the Keys. There were many excellent restaurants in the area when you wanted to go out, and a full kitchen when...
See all reviews
From
$207
Per Night
1 / 26
3 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
ENTERED VACATION RENTAL MARKET: NOVEMBER 26, 2014 Welcome to SOL Y MAR SOL Y MAR offers 2,500Sq.Ft. of Living Space,Three (3) Bedrooms, Two (2) Bathrooms on Three (3) Levels. The Property is located in the Center of the Florida Keys, Tavernier, 1.5 Hours to Miami, 1.5 Hours to Key West;... View all property information
Make Enquiry
From
$2,066
Per Week
1 / 13
Payment Protection
Studio, 1 Bathroom, Sleeps 2
Details Reviews (24) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
PLEASE DO NOT TRY TO BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry. 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! You can now pay for your stay using... View all property information
Make Enquiry
5 of 5 stars Reviewed 17 November 2014
We spent 4 nights. We just loved it. It is everything as advertised. The place is small, but so clean and neat and romantic. Great info in a binder that was thoughtfully prepared...
5 of 5 stars Reviewed 8 September 2014
Had a very relaxed we here with my partner just chilling out and doing very little except lying on the hammock watching the parrot fish swim by. The hosts are great friendly...
See all reviews
From
$163
Per Night
1 / 9
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Heated Pool
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This comfortable, country-style cottage is located in Plantation Key Colony, a quiet family neighborhood at mile marker 90, bayside, on Plantation Key, the northernmost key of the seven keys that comprise Islamorada, "The Village Of Islands". It is a three bedroom, three bath home: the master... View all property information
Make Enquiry
From
$383
Per Night
1 / 30
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Come enjoy a slice of paradise in this beautiful ocean front property settled in a private, gated and lushly landscaped community. Take it all in, from the breathtaking ocean views, to the serene swimming pool, it's like a tropical dream come true. In addition to the pool this community features 2... View all property information
Make Enquiry
5 of 5 stars Reviewed 5 May 2014
This vacation rental exceeded our already high expectations! We are a family of 4 adults and 3 children familiar with staying at Hawks Cay for our prior Easter vacations. We were...
5 of 5 stars Reviewed 11 March 2014
We exchanged to this Property through Club Paradiso which is based in Tenerife. We were in property 126, which is situated in the middle row of the complex.We had sea views from...
See all reviews
From
$14,582
Per Night
1 / 1
10 Bedrooms, 10 Bathrooms, Sleeps 28
Details Reviews (12) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Got a large group that wants to "get away from it all"? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide... View all property information
Make Enquiry
5 of 5 stars Reviewed 18 October 2014
We stayed at the Alligator Reef Luxury estates as a group of 18 people. This was a business gathering to bring our team together from all over the world, and this estate couldn’t...
5 of 5 stars Reviewed 5 October 2014
We wanted a simple wedding and then a week of fun with family and friends. Alligator Reef exceeded our expectations. We had a wedding ceremony with 25 guests under the palm...
See all reviews
From
$1,943
Per Night
1 / 33
Payment Protection
4 Bedrooms, 5 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen, snorkel in the backyard!!!! Seven Flat Screens and entire house wired for sound.... View all property information
Make Enquiry
From
$5,954
Per Week
1 / 29
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Private Pool
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the... View all property information
Make Enquiry
5 of 5 stars Reviewed 23 August 2011
This property is a collection of 4 houses, 2 closer to the ocean, each with their own pool and three bedrooms (Conch and Pelican Houses), the other two behind, with no pool and...
See all reviews
From
$6,076
Per Month
1 / 26
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
A quaint bungalow on a not-so-quaint piece of oceanfront land right in the Heart of Islamorada! This home has two bedrooms, two bathrooms, and a lot of Keysy charm. During your stay, you will enjoy such amenities as a fishing dock with Chickee hut (1ft draft), cable television, a kayak, and a white... View all property information
Make Enquiry
From
$6,805
Per Month
1 / 17
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Minimum Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It is located on a... View all property information
Make Enquiry
From
$920
Per Night
1 / 40
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (16) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Private Pool
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
Make Enquiry
2 of 5 stars Reviewed 29 April 2014
Everything seemed to be broken. The pool water had a green tint and was finally shocked by the pool guy. One of the closet doors was broken off and placed in the closet. One of...
3 of 5 stars Reviewed 3 December 2013
Yes, the house is great for large family but the amenities leave something to be desired. Appliances are dated, counter tops are tiled and grout appears dirty. Washer broke, oven...
See all reviews
Enquire for rates
1 / 11
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
****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... View all property information
Make Enquiry
5 of 5 stars Reviewed 17 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...
See all reviews
From
$146
Per Night
1 / 25
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (16) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen television, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
Make Enquiry
5 of 5 stars Reviewed 9 December 2014
this condo is really great for two People. The Retreat is quite (allthough directly located at the overseas Highway), the condo is towards Bay and the small marina. The condos...
5 of 5 stars Reviewed 12 August 2014
My wife and I stayed a week at the Florida Bayside retreat and absolutely loved it. The condo was extremely clean and had a great view of the water. My wife and I also were...
See all reviews
From
$179
Per Night
1 / 18
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Heated Pool
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Enjoy your vacation in this recently remodeled 2 bedroom 2 bath Condo. Just off the living room and master bedroom, you can sit on your balcony that looks over the crystal clear waters of the Atlantic and the marina. There are lots of things to do in the complex from swimming in the pool, relaxing... View all property information
Make Enquiry
3 of 5 stars Reviewed 9 April 2013
We were going to bring our boat down from Miami but when we found out the hotel charges $3.00 per foot per day, we found that to be quite excessive...we are guests! One would...
See all reviews
From
$3,369
Per Month
1 / 29
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Beautiful three bedroom bay side townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World.... View all property information
Make Enquiry
5 of 5 stars Reviewed 27 October 2014
We never did a vacation rental before and it was Great. Place had everything we needed and had enough space for our large group! It was also clean. Pool was big and nice! we...
5 of 5 stars Reviewed 19 July 2014
Would suggest having map of condo development for first time visitors. If items were missing or needing repair, received excellent response time. Patio chairs need replacing...
See all reviews
From
$122
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Heated Pool
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
Make Enquiry
Enquire for rates
1 / 47
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (3) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Sauna
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
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,... View all property information
Make Enquiry
2 of 5 stars Reviewed 22 August 2013
In addition to my wife's comments there is another thing a prospective renter must take into consideration: the lease agreement states that any disputes with the rental agent be...
2 of 5 stars Reviewed 13 August 2013
My husband and I recently rented this condo for a 3-night dive trip with our 2 boys, ages 17 and 19. While the condo itself was clean, the building was old and the parking lot was...
See all reviews
From
$6,076
Per Month
1 / 21
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. We are located on Lower Matecumbe Key just a few miles south of the hustle and bustle of downtown Islamorada. This is a spacious three bedroom with vaulted ceilings, a... View all property information
Make Enquiry
5 of 5 stars Reviewed 19 November 2014
We stayed at Captains Cove again for our annual fishing weekend. Cindy, the new owner, has made several updates to the house, deck and dock which enhanced the property since our...
See all reviews
From
$120
Per Night
1 / 23
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Internet Access
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
87200 Overseas Hwy Islamorada, Florida An ample 1,400 sq ft. town home in the heart of Islamorada. Two bedrooms and one bathroom upstairs. One bedroom has two queen beds and cable television. Second bedroom is set up with one queen bed and cable television. Sofabed and bathroom downstairs.... View all property information
Make Enquiry
From
$314
Per Night
1 / 21
Payment Protection
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 September 2014
Looked far and wide for a place in the keys that was on one level for my mom that uses a walker. Finally found the one! The owner is very helpful and communicative and worked...
5 of 5 stars Reviewed 25 January 2014
This condo exceeded our expectations. It was truly a home away from home. It has all the amenities you will need to have a great vacation. The kitchen is fully furnished, the...
See all reviews
From
$1,823
Per Week
1 / 22
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
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... View all property information
Make Enquiry
4 of 5 stars Reviewed 16 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...
See all reviews
Enquire for rates
1 / 8
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This pretty, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a pretty upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is additional tidy and modernly furnished.... View all property information
Make Enquiry
3 of 5 stars Reviewed 8 November 2014
The pictures of the home were pretty accurate although the canal it sits on offers no added feature, not used by anyone, no dock, swimming or view of boats. Home had bare minimum...
5 of 5 stars Reviewed 14 July 2013
The Perfect Getaway is an appropriate name for this house; it had everything needed for a perfect vacation getaway in the Keys. The pool and hot tub were great to cool off from...
See all reviews
From
$1,033
Per Night
1 / 7
Payment Protection
8 Bedrooms, 6 Bathrooms, Sleeps 16
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Keys Oceanfront Estate The Florida Keys largest and most presteges home A peaceful and picturesque mansion awaits you and your loved ones in Islamorada, Florida. Grab your rod and reel, for an afternoon of casting right off the dock. Enjoy the abundance of nature right outside your door while you... View all property information
Make Enquiry
5 of 5 stars Reviewed 27 March 2014
The house was amazing! Just as the pictures show. We were traveling with 4 adults and 6 teenagers. There was always something for everyone to do. The property manager was friendly...
See all reviews
From
$972
Per Night
1 / 45
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
* 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)... View all property information
Make Enquiry
From
$365
Per Night
1 / 29
Payment Protection
2 Bedrooms, 3 Bathrooms, Sleeps 5
Details Reviews (22) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
Make Enquiry
5 of 5 stars Reviewed 21 August 2014
We fell in love with the villa the minute we walked in through the door. Everything was immaculate and extremely welcoming. The owner had thought about everything and the box of...
5 of 5 stars Reviewed 30 June 2014
This was the perfect place for a relaxing vacation with my extended family. The location was great, and close to all Islamorada has to offer. The pool was so nice, overlooking the...
See all reviews
From
$3,646
Per Month
1 / 23
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Balcony
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity to... View all property information
Make Enquiry
5 of 5 stars Reviewed 14 August 2014
Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.
See all reviews
From
$4,861
Per Month
1 / 26
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Grill
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
MINIMUM RENTAL: 1 MONTH BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This is a completely remodeled 3 bedroom/2 bath (2/1 up and 1/1 down) single family home - perfect for one couple or a smaller family. It is conveniently located in... View all property information
Make Enquiry
From
$157
Per Night
1 / 21
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
Make Enquiry
From
$157
Per Night
1 / 26
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
Make Enquiry
From
$348
Per Night
1 / 26
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
Make Enquiry
From
$400
Per Night
1 / 25
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
Make Enquiry
4 of 5 stars Reviewed 5 June 2014
This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
4 of 5 stars Reviewed 24 June 2013
Have been going to Islamorada for years and this year planned a trip with 4 other friends and our dog. This was the perfect house. plenty of room for all of us. The views are...
See all reviews
Enquire for rates
1 / 17
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
****This house cannot rent for less than 28 days, per County Ordinance**** Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Oasis. Oasis is located at Mile Marker 75.6, in beautiful Islamorada. This Beautiful three bedroom, three bath home will sleep 8 people very Comfortably. Besides the... View all property information
Make Enquiry
From
$5,468
Per Month
1 / 23
3 Bedrooms, 1 Bathroom, Sleeps 1
Details Reviews (4) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
A very charming and immaculate 3 bedroom home in Plantation Key. This home has excellent protected deep water dockage. Ocean views from balcony. Easy bay access via Tavernier Creek. Close to resturants and store. CLICK HERE to view photos on a mobile device. Additional amenities include:... View all property information
Make Enquiry
From
$4,861
Per Month
1 / 26
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This home, located in the Plantation Key Colony neighborhood, is a fantastic home for a family or just a couple who wants to enjoy an escape to the Florida Keys. Home is located on a canal with 50ft of concrete dockage, along with a fish cleaning station. The yard is completely fenced in, has a... View all property information
Make Enquiry
From
$521
Per Night
1 / 11
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
Make Enquiry
4 of 5 stars Reviewed 13 August 2014
The home that we stayed at was incredible! The accommodations, the view, the boat dock space was all great. It was fast in and out to the Atlantic Ocean to be able to scuba...
5 of 5 stars Reviewed 5 January 2013
We stayed here for Christmas with 6 people (using 4 bedrooms). The main house has 3 bedrooms and the mother-in-law apartment across the deck has 2 bedrooms as well as a kitchen...
See all reviews
From
$348
Per Night
1 / 15
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (6) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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.... View all property information
Make Enquiry
From
$365
Per Night
1 / 9
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a... View all property information
Make Enquiry
Go to map view
Rental communities
Nearby rentals
Book Online(22)
Use filters to find the best results!

Suitability

  • Wheelchair access (12)
  • Elder access (31)
  • Suitable for children (33)
  • Pet friendly (32)
  • Smoking allowed (2)

Amenities

  • Grill (121)
  • Internet (118)
  • Air Conditioning (106)
  • Other outdoor space (106)
  • All pools (79)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List