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.

Islamorada Rentals with Pools

List your property
Owner log in
Where to?
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 mi
225 rentals in Islamorada.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

109 Anglers Way
Lovely path leading to the pool.
Luxurious Home at beautiful Anglers Reef with Boat Slip available
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Direct Oceanfront Views In Anglers Reef, Islamorada. Resort Pool, Dock, Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef
Rental Home
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2 Sleeps 6
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Brand New / Totally Renovated Luxurious Home New To Rental Market.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Paradise in Venetian Shores w New Pool / SPA.....Commercial Ice Maker! !!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Save time - get the best Islamorada rentals sent straight to your email!
A little Piece of Heaven to wash your worries away
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

BROCK HAUS ON THE GULF
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out

�AQUAMARINE=OCEANVIEW�SALE AUG 13-27 $247 nite w/DOCK+2 MASTERS+ 1,700 sq feet
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Anglers Reef Islamorada*Bikes*Kayak*Paddle Boards*DOCK* available-Pool
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Mitchell's Bayview Villa - Islamorada House on the Bay
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Anglers Reef- Fall Discount
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Private Tropical Oceanfront Estate with Pool and Beach
Rental Home
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Iconic Ted Williams Estate. Waterfront,Dock,Amazing Pool & Spa,Walk to Lorelei.
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

7 Bedroom with Dockage - Pool, Paddle Boards, Kayaks included
Rental Home
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Bayside Condo, marina, pool and beach
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Your PRIVATE OCEANFRONT ESTATE awaits! Gorgeous 5 Bedroom Home with Infinity Poo
Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Oceanfront Condo: Ocean Views, Pool, WIFI
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - B
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Newly refinished condo open water views very nice
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Oceanfront Oasis - Pinch me am I dreaming!!!
Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

BEACON REEF 310
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check in
Check out

Butterfly Haven - Beautiful Bayfront Home with Cottage
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Angler's Reef- Oceanside Resort... Oceanview unit with kayaks, paddleboards and
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

The PERFECT Escape with pool & jacuzzi
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Peaceful 2 Bedroom Oceanfront Cottage with Pool and Dock
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Luxury condo overlooking harbor with ocean view
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Beautiful Maison #307
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Pristine Pool Front Anglers Reef w/ Ocean Views, Private Beach & Dock
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Bay Front Beauty/ Summer Sea Must See!!!!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

A Good Stay ~ Islamorada Waterfront Residence
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Cheerful Anglers Reef Home in Islamorada with kayaks + pool on Atlantic Ocean
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Bay Views from this Charming 2 Bedroom Condo - Futura Townhome 708
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Redecorated Islamorada gem in beautiful Angler's Reef is ready for you!
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

PALMS 309
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
Check in
Check out

3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Angler's Reef #118 - Charming 2 Bedroom House with Peekaboo Views
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Maison Matecumbe #303 - 3 Bedroom Oceanfront Townhome in Premier Gated Complex
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

PreviousNext
12345