Islamorada Vacation Rentals
Destination
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 mi
744 rentals in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
ULTIMATE outdoor living area at this 4/4 canal home with pool!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
New Rental! Beautiful canal pool home with dockage!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
You will never want to leave
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Charming Islamorada house with waterfront, private dock and beach
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
3 BR 2 Bath Islamorada home with Private Beach Access
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Mini Ray's of Sunshine
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
This is The Oasis, YOUR private Oasis!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Your Retreat in the Heart of Islamorada! Kitchenette, Outdoor Swimming Pool!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Oceanfront Property w/ Outdoor Pools, Pets Allowed, Free Parking Onsite
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
The Bonefish House at Tarpon Point
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
SALT HAVEN - BEAUTIFUL & CLEAN 70' WATERFRONT/CANAL POOL HOME + PRIVATE BEACH
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
This studio makes the best of the space
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Beautiful 3 Bedroom Condo - Bay Harbour A101
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Charming 2 Bedroom House with Peekaboo Views
More info
Check in
Check out
As seen on
Oceanfront Oasis in Angler’s Reef with Private Boat Slip
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Steps Away from the Beach | Spacious 1BR Suite w/ Kitchenette
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
" Endless Summer" Awaits!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
La Casita White Marlin
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
A True Islamorada Oasis with Breathtaking Bay Views
More info
Check in
Check out
As seen on
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Snorkeling in Islamorada! Premium Villa, Bike Rentals & Water Sports Equipment!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
More info
Check in
Check out
As seen on
Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!
Rental Home
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Cosy Cottage in Islamorada with private garden & pool - 6 pers.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Oceanview 2b/2b w/ Boatslip
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Discover the Charm of Island Living
More info
Check in
Check out
As seen on
Beautiful vacation home in the heart of Islamorada , Florida Keys
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
4 Units Perfect for Big Groups! Beachfront Property with Outdoor Pools!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
As seen on
Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Bayside Tranquility: 3 Relaxing Villa w/ Spacious Living Area & Kitchen
Rental Home
6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Check in
Check out
As seen on
Peaceful 2 Bedroom Oceanfront Cottage with Pool and Dock
More info
Check in
Check out
As seen on
Enjoy a Hassle-Free Stay! Free Parking, Onsite Pool, Near Anne's Beach
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
3 Bedroom Private Oceanfront House - Sol
More info
Check in
Check out
As seen on
Little Piece of Paradise (AVAIL Oct-Dec)
Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Luxurious Caribbean 2 Bedroom 2 Bath Home
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Maison Matecumbe.... the heart of Islamorada!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Your Keys Getaway - A
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, Free Parking!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna
Condo/Apartment
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Sun, Ocean and a Luxury Oasis with a discount Flexible stays contact host
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Beautiful oceanfront resort located at mile marker 73.8
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
AQUAMARINE OCEANVIEW<-WALL to WALL->+143 BEST 5 STAR REVIEWS+DOCK+POOL+GYM++++++
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Showing results 1-50 of 744
Frequently Asked Questions about Islamorada
- Yes, here are some popular vacation rentals in Islamorada that have a pool:
- Ocean Front Town House With Breath Taking Views From all 3 Balconies
- Wonderful 2 Bedroom Condo with Ocean Views
- ULTIMATE outdoor living area at this 4/4 canal home with pool!
- Yes, here are some popular vacation rentals in Islamorada that have internet access:
- Wonderful 2 Bedroom Condo with Ocean Views
- ULTIMATE outdoor living area at this 4/4 canal home with pool!
- Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside
- The best pet friendly rentals in Islamorada are:
- ULTIMATE outdoor living area at this 4/4 canal home with pool!
- Pets are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, Pool
- Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock
- Some of the most popular kid friendly rentals in Islamorada are:
- Wonderful 2 Bedroom Condo with Ocean Views
- ULTIMATE outdoor living area at this 4/4 canal home with pool!
- Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside
Islamorada TourismIslamorada HotelsIslamorada Bed and BreakfastIslamorada Vacation RentalsFlights to IslamoradaIslamorada RestaurantsThings to Do in IslamoradaIslamorada Travel ForumIslamorada PhotosIslamorada MapIslamorada Travel Guide
All Islamorada HotelsIslamorada Hotel DealsLast Minute Hotels in Islamorada
Things to DoRestaurantsFlightsIslamorada MotelsIslamorada CampgroundsIslamorada Family HotelsIslamorada Beach HotelsIslamorada ResortsRomantic Hotels in IslamoradaIslamorada Green HotelsIslamorada Business HotelsIslamorada Luxury HotelsIslamorada Spa Resorts
Budget Hotels in IslamoradaSuite Hotels in IslamoradaBeachfront Hotels in IslamoradaFishing Resorts in IslamoradaIslamorada Hotels with KitchenetteDiving Resorts in IslamoradaIslamorada Luxury Boutique HotelsHotels with Villas in IslamoradaRomantic Boutique Hotels in IslamoradaRomantic Bed and Breakfast in Islamorada
Vacation Rentals near Windley Key Fossil Reef Geological State ParkVacation Rentals near Robbie's of IslamoradaVacation Rentals near Florida Keys Dive CenterVacation Rentals near Rain Barrel VillageVacation Rentals near Founders ParkVacation Rentals near Key Largo Bicycle and Adventure ToursVacation Rentals near Islamorada Dive Center