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
.
Flights
Holiday Rentals
Restaurants
Things to do
Skip to main content
Discover
Trips
Review
More
GBP
Sign in
Islamorada
Hotels
Things to Do
Restaurants
Flights
Holiday Rentals
Cruises
Car Hire
Forums
Inbox
See all
Log in
to get trip updates and message other travellers.
Holiday Rentals with Pools in Islamorada
Holiday Rentals
USA
Florida (FL)
Florida Keys
Islamorada
Rentals with Pools in Islamorada
Search
Owner log in
Islamorada
Holiday Rentals with Pools
Destination
Check In
Check Out
Guests
2 Guests
Map
Tripadvisor Sort
Revenue impacts this sort order.
Learn more
Bedrooms
Any
Bathrooms
Any
Amenities
All pools (1)
Public pool (1)
Internet or Wifi (1)
Sauna (1)
Show all
Suitability
Kid friendly (1)
Wheelchair access (0)
Elder access (0)
Pet friendly (0)
Show more
Property type
Condominium/Apartment (1)
Holiday Rental House (0)
Cabin Holiday Rental (0)
Private Room (0)
Show more
Distinctive Features
Private Chef (0)
Private Beach (0)
Waterfront (0)
Ski In/Ski Out (0)
Show all
Distance from
5 mi
History of Diving Museum
Florida Keys Brewing Company
Islamorada Brewery & Distillery - MM82
Alligator Reef Light House
Windley Key Fossil Reef Geological State Park
Show all
1 rental
in Islamorada.
Ocean Front Town House With Breath Taking Views From all 3 Balconies
Condo/Apartment
View on map
0 bedrooms
0 bathrooms
Sleeps 8
Match:
Sleeps, All pools
More info
Check-in
Check-out
Show Prices
As seen on
The following properties match some of your filters:
Wonderful 2 Bedroom Condo with Ocean Views
3
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Adorable canal front Pool Home in Plantation Key
3
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
ULTIMATE outdoor living area at this 4/4 canal home with pool!
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
"Our Happy Place" Paradise in Islamorada with Heated Pool and 90 ft Dock
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
Holiday Rental House
View on map
9 bedrooms
10 bathrooms
Sleeps 18
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Stunning 3 Bedroom Bayfront Home
2
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
3
Holiday Rental House
View on map
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Better Choice for your Vacation! 2 Comfortable Units, Beachfront, Outdoor Pool
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
3 bedroom, 3.5 bath luxurious condo 402 at Maison in Islamorada
Condo/Apartment
View on map
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Executive Bay - Next to Beach and Pool!
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock.
Holiday Rental House
View on map
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Your Idyllic Getaway Awaits! Breathtaking Beachfront, Outdoor Pool | 3 Units
Holiday Rental House
View on map
6 bedrooms
6 bathrooms
Sleeps 18
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Ultimate Beach Relaxation: Resort w/ Marina and Outdoor Pool | Free Parking
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Harbor Hideaway | Island style beach house with pool, dockage & bay views!
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Charming Condo in Paradise!
Condo/Apartment
View on map
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.
5
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
NEW! Delightful 2 Bedroom Townhouse with Pool, Beach, Tennis Courts & More
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Private Pool, Completely Renovated Lovely Cottage Home in Islamorada
10
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Deluxe upper apartment with pool, canal-view balcony, water access, grill, & AC
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Pool | Sunsets | Walk to restaurants | Little Basin Villas | Conch Villa 6
10
Holiday Rental House
View on map
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Cozy Studio on Oceanfront Property with Pool
11
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Spectacular Coastal Paradise with outstanding outdoor living spaces
Holiday Rental House
View on map
5 bedrooms
7 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Captain's Quarters Piece of Peace
1
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
1
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Modern ground-floor apartment with pool, water views, patio, grill, & central AC
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Fabulous " Sea Breeze 41 ", 3 / 2 Condo located Oceanside in Islamorada
Condo/Apartment
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Island Oasis in Islamorada: Your Private Paradise Awaits!
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
159
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
You Don’t Want to Miss This! Beachfront, Onsite Pool, Near Coral Bay Marina
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Your Blissful Haven in Islamorada! Beach, Swimming Pool, Pets Allowed!
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Beautiful Maison #307
10
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Paradise Found - Three Story Beach House w/ private beach, dock and Ocean Views
13
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
At The Sandbar: Oceanfront, Htd Pool, Dock, GameRoom, EV Charger
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Your Retreat in the Heart of Islamorada! Kitchenette, Outdoor Swimming Pool!
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Isla Honeydew: 3 En-Suite Bedrooms! Waterfront Resort, Pool, Dock!
Holiday Rental House
View on map
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Beautiful 3 Bedroom Condo - Bay Harbour A101
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Breathtaking Bayfront Villa w/ Private Patio & Living Area, Perfect For Couple
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Charming 2-bedroom house in welcoming Islamorada with WiFi, AC
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Endless Paradise at Executive Bay Club in Islamorada
10
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Relax in this gorgeous townhome while overlooking the sparkling Atlantic Ocean
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Escape to MarchettiVille Your Own Private Oasis
Holiday Rental House
View on map
5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental
Condo/Apartment
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Beautiful estate nestled in a secluded cove on the ocean, 60 ft dock, guesthouse
Holiday Rental House
View on map
5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Indulge in Home Like Comfort! Oceanfront, Free Parking, Pet-friendly Property
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Ocean View with protected dock on lagoon with private boat ramp
10
Condo/Apartment
View on map
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Safety harbor seasonal fishing getaway with room for 12
Holiday Rental House
View on map
7 bedrooms
5 bathrooms
Sleeps 15
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage
Condo/Apartment
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
1
2
…
17
Showing results 1-50 of 814
Islamorada
Islamorada Tourism
Islamorada Hotels
Bed and Breakfast Islamorada
Islamorada Holiday Rentals
Flights to Islamorada
Islamorada Restaurants
Islamorada Attractions
Islamorada Travel Forum
Islamorada Photos
Islamorada Map
Islamorada Guide
Hotels
All Islamorada Hotels
Islamorada Hotel Deals
Last Minute Hotels in Islamorada
By Hotel Type
Islamorada Motels
Islamorada Campsites
Islamorada Resorts
Romantic Hotels in Islamorada
Islamorada Beach Hotels
Family Hotels Islamorada
Islamorada Green Hotels
Luxury Hotels in Islamorada
Business Hotels Islamorada
Spa Hotels in Islamorada
By Hotel Class
5-stars Hotels in Islamorada
4-stars Hotels in Islamorada
3-stars Hotels in Islamorada
Popular Amenities
Islamorada Hotels with a Pool
Pet Friendly Hotels in Islamorada
Popular Islamorada Categories
Budget Hotels in Islamorada
Islamorada Accessible Hotels
Islamorada Shopping Hotels
Islamorada Exotic Resorts
Islamorada Exotic Hotels
Islamorada Yoga Resorts
Islamorada Windsurfing Resorts
Islamorada Snorkelling Resorts
Islamorada Resorts with Boats
Islamorada Yoga Hotels
Near Airports
Hotels near (MIA) Miami Intl Airport
Things to Do
Restaurants
Flights
Holiday Rentals
By Holiday Rental Type
Apartment Rentals in Islamorada
Cheap Islamorada Holiday Rentals
Islamorada Luxury Holiday Rentals
Popular Amenities
Pet Friendly Rentals in Islamorada
Kid Friendly Islamorada Holiday Rentals
Places of Interest
Holiday Rentals near Windley Key Fossil Reef Geological State Park
Holiday Rentals near Robbie's of Islamorada
Holiday Rentals near Florida Keys Dive Center
Holiday Rentals near Rain Barrel Village
Holiday Rentals near Founders Park
Holiday Rentals near Key Largo Bicycle and Adventure Tours
Holiday Rentals near Islamorada Dive Center
Travel Stories
Cruises
Car Hire
More
Tours
Add a Place
Travel Forum
Airlines
Travellers' Choice
Help Centre
Travel Stories