search location
Travel Dates:
Reset Dates
1,000 Rentals In Islamorada
United States
Florida
Monroe Area
Florida Keys
Islamorada
Filters
Guests
Guests
1
2
3
4
5
6
7
8+
Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
Islamorada Ocean Views\nNew 2\/2 Waterfront bars\/restaurants\/shopping close by\n
2
2.0
5
Islamorada Florida Mobile home
From $90 per night
(USD)
☀️Luxury 3 BR Remodeled! Ocean View, Pool Spa, Marina Bikes Kayak Tennis\/Pickle
3
3.0
6
Islamorada Florida Condo
From $573 per night
(USD)
Beautiful New Island Home for 2 Small Families
5
3.0
8
Tavernier Florida Private vacation home
From $575 per night
(USD)
Tropical Paradise at Futura Yacht Club
2
2.0
6
Tavernier Florida Condo
From $215 per night
(USD)
Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe
3
3.0
6
Islamorada Florida Private vacation home
From $477 per night
(USD)
Alligator Reef Conch & Lobster Homes, a special slice of paradise
5
5.0
14
Islamorada Florida Private vacation home
From $1097 per night
(USD)
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
2
3.0
6
Islamorada Florida Private vacation home
From $509 per night
(USD)
Canal front Oasis with Pool and Tiki Hut
3
2.0
6
Tavernier Florida Private vacation home
From $198 per night
(USD)
Seaside Sanctuary 5 bed, 5 bath pool home
5
5.0
10
Tavernier Florida Private vacation home
From $1000 per night
(USD)
Waterfront Pool Home with great dockage!
3
3.0
6
Tavernier Florida Private vacation home
From $320 per night
(USD)
Paradise Retreat
3
3.0
8
Islamorada Florida Private vacation home
From $450 per night
(USD)
POOL AND DEEP WATER DOCK
3
2.0
6
Islamorada Florida Private vacation home
Click For Pricing
Front Row, DIRECT Ocean\/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
2
3.0
6
Islamorada Florida Private vacation home
From $514 per night
(USD)
Cute Canal front Venetian Shores Weekly Rental!
3
2.0
4
Islamorada Florida Private vacation home
From $496 per night
(USD)
Bay Views from this Charming 3 Bedroom Canal Home
3
3.0
6
Tavernier Florida Private vacation home
From $198 per night
(USD)
Panoramic Ocean Views from this 3 Bedroom Islamorada Home
3
3.0
6
Islamorada Florida Private vacation home
From $469 per night
(USD)
Home in Islamorada Florida
4
3.0
12
Tavernier Florida Private vacation home
From $365 per night
(USD)
Cheerful 4bedroom and 4 1\/2 bath
4
5.0
8
Tavernier Florida Private vacation home
Click For Pricing
Little Piece of Paradise (AVAIL Oct-Dec)
3
1.0
8
Islamorada Florida Private vacation home
Click For Pricing
Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more
2
1.0
5
Islamorada Florida Private vacation home
From $572 per night
(USD)
Unique 2 Bedroom Bay Front Home with Roof Top Terrace
2
2.0
4
Islamorada Florida Private vacation home
From $373 per night
(USD)
Quiet Home Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+2 Kayaks+2 Offices
3
2.0
6
Islamorada Florida Private vacation home
From $295 per night
(USD)
Renovated canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.
4
3.0
8
Tavernier Florida Private vacation home
From $700 per night
(USD)
Work remote, or not at all, in paradise at this cozy, beachy condo!
2
2.0
6
Tavernier Fl Condo
From $180 per night
(USD)
Beautiful 'Keysey' Condo in Gated Community 24-0169
2
3.0
4
Islamorada Florida Condo
From $308 per night
(USD)
Islamorada Luxury Waterfront Condo with Boat Slip
2
3.0
6
Islamorada Florida Condo
From $339 per night
(USD)
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
2
3.0
4
Islamorada Florida Condo
From $315 per night
(USD)
Oceanfront! Oceanfront! Oceanfront!
2
2.0
4
Tavernier Florida Condo
From $325 per night
(USD)
Discover the Charm of Island Living
2
2.0
4
Islamorada Florida Condo
From $237 per night
(USD)
Penthouse view - Futura Yacht Club #604
3
2.0
5
Tavernier Florida Condo
From $209 per night
(USD)
Executive Bay Club Condo (2 bds + loft & 3 full baths)
2
3.0
9
Islamorada Florida Private vacation home
From $175 per night
(USD)
A great place to relax, fish, or even work from. 2\/2 , 66 ft
2
2.0
7
Tavernier Florida Private vacation home
Click For Pricing
Beautiful Bayfront Home with Amazing Sunsets
4
3.0
8
Islamorada Florida Private vacation home
From $700 per night
(USD)
Spectacular Top Floor Oceanfront View Condo
1
1.0
2
Plantation Key Florida Condo
From $142 per night
(USD)
Private Pool, Completely Renovated Lovely Cottage Home in Islamorada
4
3.0
8
Islamorada Florida Private vacation home
From $514 per night
(USD)
Super Penthouse - Futura Yacht Club #603
2
2.0
4
Tavernier Florida Condo
From $400 per night
(USD)
4 BR Ocean front Condo in Islamorada, FL Keys steps away from pool & sandy beach
4
5.0
8
Islamorada Florida Condo
From $2571 per night
(USD)
OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
1
1.0
4
Islamorada Florida Villa
From $239 per night
(USD)
Ocean Front 4 Bedroom Estate with Private Beach
4
5.0
12
Islamorada Florida Villa
From $1643 per night
(USD)
5 Bedroom Ocean Front Pool Home
5
5.0
10
Islamorada Florida Villa
From $1429 per night
(USD)
Beautiful Townhouse in the heart of the Florida Keys
2
2.0
10
Islamorada Florida Private vacation home
From $130 per night
(USD)
Pineapple Point pet friendly paradise Islamorada\n\n
2
2.0
6
Tavernier Florida Mobile home
From $150 per night
(USD)
Islamorada 3\/2 condo. Dockage, swimming pool, sunsets
3
2.0
6
Islamorada Florida Condo
From $292 per night
(USD)
Incredible Bayside Home in the Florida Keys!
3
3.0
8
Islamorada Florida Private vacation home
From $305 per night
(USD)
Family\/Pet Friendly Venetian Shores Home
3
2.0
6
Islamorada Florida Private vacation home
From $402 per night
(USD)
Bright & Cheery Pool Front Home with Ocean Views at Anglers Reef in Islamorada
2
3.0
6
Islamorada Florida Private vacation home
From $450 per night
(USD)
Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach
4
3.0
8
Islamorada Florida Private vacation home
From $750 per night
(USD)
Just a Few Friends - Ocean View and Bring your Boat!
2
3.0
4
Islamorada Florida Condo
From $292 per night
(USD)
Waterfront Oasis Legal weekly rental*Mins2Beach*Tons of dockage
5
3.0
12
Islamorada Florida Private vacation home
From $929 per night
(USD)
BAYSIDE PARADISE ~ Heart of Islamorada ~ Private Boat Dockage
4
4.0
8
Islamorada Florida Private vacation home
From $821 per night
(USD)
Indian Mound - Islamorada Keys Bungalow
3
2.0
8
Tavernier Florida Private vacation home
From $175 per night
(USD)
Charming 2 Bedroom Condo in Wonderful Beacon Reef
2
2.0
4
Islamorada Florida Private vacation home
From $162 per night
(USD)
Aqua Lodge Houseboat \"The Grey Lady\"
4
2.0
6
Tavernier Florida House boat
From $500 per night
(USD)
Aqua Lodge Houseboat \"Sea Turtle\"
1
1.0
2
Tavernier Florida House boat
From $333 per night
(USD)
Aqua Lodge Houseboat \"Calypso\"
3
2.0
6
Tavernier Florida House boat
From $456 per night
(USD)
Aqua Lodge Houseboat \"Captain's Quarters\"
2
1.0
4
Tavernier Florida House boat
From $390 per night
(USD)
Private Tropical Oasis
1
1.0
2
Islamorada Florida Apartment
From $180 per night
(USD)
Venetian Shores Pool Home
4
3.0
6
Islamorada Florida Private vacation home
Click For Pricing
Aqua Lodge Houseboat \"Yellow Tail \"
1
1.0
5
Tavernier Florida House boat
From $356 per night
(USD)
Aqua Lodge Houseboat \"Tarpon\"
1
1.0
5
Tavernier Florida House boat
From $356 per night
(USD)
Beautifully Updated Studio Apartment, Summer Sea Condo
1.0
2
Tavernier, Florida Condo
From $106 per night
(USD)
Luxury Oceanfront Villa with Resort Amenities
4
5.0
8
Islamorada Florida Villa
From $2390 per night
(USD)
Radiant Suite with Ocean View and Resort Amenities
1
1.0
4
Islamorada Florida Guest house
From $696 per night
(USD)
Alluring Accessible Suite with Ocean Views
1
1.0
4
Islamorada Florida Guest house
From $683 per night
(USD)
Pristine Accessible Oceanfront Villa at Islamorada
4
5.0
8
Islamorada Florida Villa
From $2164 per night
(USD)
San Remo Canal Front
5
4.0
10
Islamorada Florida Private vacation home
From $467 per night
(USD)
Ocean Views from Balcony, Living Room and Bedroom. Islamorada License 24-0380
1
1.0
2
Tavernier \/ Islamorada fl Condo
From $156 per night
(USD)
THE premier gated oceanfront complex in the heart of Islamorada.
3
2.0
6
Islamorada Florida Condo
From $562 per night
(USD)
Paradise Found - Three Story Beach House w\/ private beach, dock and Ocean Views
3
3.0
6
Islamorada Florida Villa
From $470 per night
(USD)
Luxury villa with beautiful bay views | Pool | Little Basin Villas | Bay Villa 9
3
4.0
6
Islamorada Florida Private vacation home
From $819 per night
(USD)
Waterfront Sunset View Aqua Villa Dolphin @ Mangrove Marina Resort
2
1.0
5
Tavernier Florida House boat
From $356 per night
(USD)
To Paradise \nBook our website fishing & excursions bigdavechartersandtours.com\n
4
2.0
14
islamorada Florida Private vacation home
From $700 per night
(USD)
Beautifully Renovated 2 Bedroom Condo
2
2.0
4
Islamorada Florida Private vacation home
From $193 per night
(USD)
Manatee Harbor - Bayfront Home on Plantation Key
4
5.0
12
Tavernier Florida Private vacation home
From $654 per night
(USD)
4 bedroom, Ocean front,Top tier Condo in Islamorada, Florida Keys
4
5.0
8
Islamorada Florida Private vacation home
From $1575 per night
(USD)
Plantation Key Colony Canal with Boat lift
2
2.0
6
Plantation Key Florida Private vacation home
From $210 per night
(USD)
Ocean Views for DAYS!
2
2.0
4
Islamorada Florida Private vacation home
From $374 per night
(USD)
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
3
3.0
6
Islamorada Florida Condo
From $521 per night
(USD)
Spring & summer dates available licensed rental vr #24-0235 NO BOATS
2
2.0
6
tavernier Florida Condo
From $157 per night
(USD)
Beautiful Cottage in Islamorada on canal front! Wifi, Smart TVs and No Stairs!
3
1.0
8
Tavernier Florida Private vacation home
From $228 per night
(USD)
Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
2
2.0
4
Islamorada Florida Private vacation home
From $172 per night
(USD)
COASTAL ELEGANCE FOR RENT IN ISLAMORADA !!! PARADISE FOUND ON DEEP WATER
3
2.0
6
Plantation Key Florida Private vacation home
From $564 per night
(USD)
Sanctuary In Paradise Featured On H G T V
4
4.0
10
Tavernier Florida Private vacation home
From $886 per night
(USD)
Relax in Islamorada-Canal Front 3 Bedroom \/ 2 Bath Home
3
2.0
6
Tavernier Florida Private vacation home
From $475 per night
(USD)
WATERFRONT KEYS COTTAGE GREAT RATES ! Walking distance to world famous Lorelei
1
1.0
2
Islamorada Florida Cottage
From $280 per night
(USD)
Egret House @ Tarpon Point
4
4.0
8
Islamorada Florida Private vacation home
From $846 per night
(USD)
Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.
5
4.0
10
Islamorada Florida Private vacation home
From $1357 per night
(USD)
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
4
3.0
10
Tavernier Florida Private vacation home
From $995 per night
(USD)
Bayfront 4 Bedroom Home on 3.5 Acre Private Estate w\/ POOL, DOCK & BEACH!
4
6.0
10
Islamorada Florida Private vacation home
From $1200 per night
(USD)
3 bed 2 bath condo at Futura Yacht Club!
3
2.0
6
Tavernier Florida Condo
From $315 per night
(USD)
OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada
5
3.0
10
Islamorada Florida Private vacation home
From $1248 per night
(USD)
Port of Call C2 - Townhome with Oceanview
2
3.0
4
Islamorada Florida Private vacation home
From $119 per night
(USD)
Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach
2
3.0
6
Islamorada Florida Private vacation home
From $542 per night
(USD)
Brand New \/ Totally Renovated Luxurious Home with POOL
3
2.0
8
Islamorada Florida Private vacation home
From $453 per night
(USD)
Charming Beach Front Home in Lower Matecumbe
4
3.0
8
Islamorada Florida Private vacation home
From $598 per night
(USD)
Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean
3
2.0
6
Islamorada Florida Private vacation home
From $344 per night
(USD)
Ultra Luxurious 4 Bedroom ocean front Rental home in Islamorada, Florida Keys
4
5.0
8
Islamorada Florida Condo
From $1658 per night
(USD)
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
3
3.0
6
Islamorada Florida Private vacation home
From $371 per night
(USD)
Beautiful 2\/2 Florida keys home rental
2
2.0
6
Islamorada Florida Private vacation home
Click For Pricing
Pool | Sunsets | Walk to Art District | Little Basin Villas | Key Lime Villa 3
3
4.0
6
Islamorada Florida Private vacation home
From $587 per night
(USD)
Load More Results