Islamorada, Florida

Vacation Rentals in Islamorada, Florida

Discover 27 vacation rental properties in Islamorada. From 1 to 5 bedrooms. Average $350/night. 100% have pools.

27 verified listings Book securely on VRBO Prices updated March 2026

27 properties available

Beautiful, sunlit home with pool, tennis court & beach access - near the marina

Beautiful, sunlit home with pool, tennis court & beach access - near the marina

2 beds 2 baths
PoolA/CWiFiBalcony
$102/night
View Details → Book on VRBO
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

3 beds 3 baths
PoolA/CWiFiBalcony
$319/night
View Details → Book on VRBO
Water-view house with private dock, washer/dryer & grill - snowbird-friendly

Water-view house with private dock, washer/dryer & grill - snowbird-friendly

2 beds 2 baths
PoolA/CWiFiBalcony
$99/night
View Details → Book on VRBO
Romantic Studio Cottage Nestled in Lush Landscaping with Pool and Dockage

Romantic Studio Cottage Nestled in Lush Landscaping with Pool and Dockage

1 bath
PoolA/CWiFiBalcony
$239/night
View Details → Book on VRBO
RELAX in your PRIVATE Oceanfront Cottage!

RELAX in your PRIVATE Oceanfront Cottage!

1 bed 1 bath
PoolA/CWiFiBalcony
$226/night
View Details → Book on VRBO
Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more

Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more

2 beds 1 bath
PoolA/CWiFiBalcony
$585/night
View Details → Book on VRBO
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

2 beds 2 baths
PoolA/CWiFiBalcony
$316/night
View Details → Book on VRBO
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip

Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip

2 beds 3 baths
PoolA/CWiFiBalcony
$392/night
View Details → Book on VRBO
Bright & Cheery Pool Front Home with Ocean Views at Anglers Reef in Islamorada

Bright & Cheery Pool Front Home with Ocean Views at Anglers Reef in Islamorada

2 beds 2 baths
PoolA/CWiFiBalcony
$375/night
View Details → Book on VRBO
Penthouse Retreat with 360* view of Ocean/Bay Rooftop Lounge

Penthouse Retreat with 360* view of Ocean/Bay Rooftop Lounge

3 beds 2 baths
PoolA/CWiFiBalcony
$178/night
View Details → Book on VRBO
OCEANFRONT ANGLERS REEF LUXURY HOME- Pool, Dock, Beach, Kayaks, Paddle Boards

OCEANFRONT ANGLERS REEF LUXURY HOME- Pool, Dock, Beach, Kayaks, Paddle Boards

2 beds 2 baths
PoolA/CWiFiBalcony
$300/night
View Details → Book on VRBO
Peacock Shores Islamorada - Vacation On The Beach!

Peacock Shores Islamorada - Vacation On The Beach!

2 beds 2 baths
PoolA/CWiFiBalcony
$309/night
View Details → Book on VRBO
Anglers Reef Islamorada home with ocean views, private marina, beach & pool

Anglers Reef Islamorada home with ocean views, private marina, beach & pool

2 beds 2 baths
PoolA/CWiFiBalcony
$326/night
View Details → Book on VRBO
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

3 beds 2 baths
PoolA/CWiFiBalcony
$678/night
View Details → Book on VRBO
Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach

Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$387/night
View Details → Book on VRBO
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

2 beds 1 bath
PoolA/CWiFiBalcony
$401/night
View Details → Book on VRBO
Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada

Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada

3 beds 2 baths
PoolA/CWiFiBalcony
$451/night
View Details → Book on VRBO
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

2 beds 1 bath
PoolA/CWiFiBalcony
$406/night
View Details → Book on VRBO
Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!

Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!

5 beds 3 baths
PoolA/CWiFiBalcony
$1,148/night
View Details → Book on VRBO
Ocean View with protected dock on lagoon with private boat ramp

Ocean View with protected dock on lagoon with private boat ramp

3 beds 2 baths
PoolA/CWiFiBalcony
$248/night
View Details → Book on VRBO
Alligator Reef Lobster House, a special slice of paradise

Alligator Reef Lobster House, a special slice of paradise

2 beds 2 baths
PoolA/CWiFiBalcony
$305/night
View Details → Book on VRBO
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

2 beds 2 baths
PoolA/CWiFiBalcony
$251/night
View Details → Book on VRBO
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

3 beds 2 baths
PoolA/CWiFiBalcony
$342/night
View Details → Book on VRBO
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach

Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$328/night
View Details → Book on VRBO
Paradise in Islamorada Venetian Shores

Paradise in Islamorada Venetian Shores

3 beds 2 baths
PoolA/CWiFiBalcony
$293/night
View Details → Book on VRBO
5 Star Modern Oceanfront Islamorada Townhome on the Beach!

5 Star Modern Oceanfront Islamorada Townhome on the Beach!

2 beds 2 baths
PoolA/CWiFiBalcony
$309/night
View Details → Book on VRBO
SUMMER SPECIAL Work from Home kids play Beach, Pool, Fishing Pier and 2 Kayaks

SUMMER SPECIAL Work from Home kids play Beach, Pool, Fishing Pier and 2 Kayaks

2 beds 2 baths
PoolA/CWiFiBalcony
$135/night
View Details → Book on VRBO

More destinations in Florida

Panama City Beach (4614) Kissimmee (3730) Davenport (2507) Miami Beach (1899) Key West (1835) Cape Coral (1809) Sarasota (1719) Marco Island (1375) Naples (1355) Siesta Key (936) Holmes Beach (770) Clearwater (768) Bradenton (551) Orlando (458) Miami (425) Anna Maria (386) Rotonda West (381) Clearwater Beach (361) Santa Rosa Beach (358) Destin (250)