Islamorada Rentals with Pools
List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighborhood
132 rentals in Islamorada.
Sort by:
Tripadvisor Sort
100' Private Beach Front Ocean Front Estate
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection
Mitchell's Keys Villa - Private, Secluded House on the Bay
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
SUNSHINE PLACE
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Luxurious Home at beautiful Anglers Reef with Boat Slip available
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
January 10% OFF! Boat Slip included, 2 Beaches, Pool, Oceanfront Anglers Reef
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Islamorada Waterfront Paradise Getaway!
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
A little Piece of Heaven to wash your worries away
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Save time - get the best Islamorada rentals sent straight to your email!
Luxurious Anglers Reef with Boat Slip, Pool, Ocean
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2 Sleeps 6
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
BROCK HAUS ON THE GULF
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Mitchell's Bayview Villa - Islamorada House on the Bay
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Bayside Condo, marina, pool and beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
75731 Overseas Highway
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Newly refinished condo open water views very nice
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Completely Remodeled 2 Bedroom, 2 Bath Florida Keys Condo On the Atlantic Ocean
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
SANCTUARY IN PARADISE
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Oceanfront Oasis - Pinch me am I dreaming!!!
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection
Luxury condo overlooking harbor with ocean view
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
BEACON REEF 310
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
140 Atlantic Lane
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Paradise Beach Sandy Oceanfront
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
132 Columbus Drive
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
THE PERFECT GETAWAY
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
82754 Overseas Highway
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
76004 Overseas Highway
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
$2500 A MONTH FOR OCTOBER AND NOVEMBER. OCEANFRONT 2 BEDROOM/2 BATH CONDO
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
137 LeSerra Lane
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Bay Front Beauty/ Summer Sea Must See!!!!
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection
Come relax in Islamorada, the tropical jewel of the Florida Keys!!
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
LITTLE BAY - Upper Duplex
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
LITTLE BAY - Lower Duplex
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
VILLA RIOLO
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Ocean-Front Caribbean Home.
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
LITTLE BAY - Cottage
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Islamorada - PARADISE FOUND 3 bedroom/2 bath
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Islamorada Waterfront Paradise 2
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
BEACON REEF 222
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
PALMS 309
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
MANATEE MANOR
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Little Bay Compound
5 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Check in
Check out
Payment Protection
Mile Marker 87 - Mina Bay - Oceanfront 'Million Dollar View'
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
107 San Remo Drive
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
123