Islamorada, Florida Vacation Rentals & Homes

See More of North America...

United States (39,376)
Canada (2,050)
Mexico (1,830)
Africa (3,080)
Asia (16,070)
Caribbean (1,553)
Central America (1,087)
Europe (30,301)
Middle East (2,927)
North America (43,266)
Pacific (2,608)
South America (4,767)

See More of United States...

Canada (2,050)
Mexico (1,830)
United States (39,376)

See More of Florida...

Alabama (713)
Alaska (675)
Arizona (888)
Arkansas (548)
California (4,217)
Colorado (1,125)
Connecticut (361)
Delaware (120)
District of Columbia
Florida (3,153)
Georgia (1,509)
Hawaii (574)
Idaho (536)
Illinois (1,086)
Indiana (779)
Iowa (473)
Kansas (412)
Kentucky (581)
Louisiana (639)
Maine (536)
Maryland (733)
Massachusetts (647)
Michigan (885)
Minnesota (585)
Mississippi (412)
Missouri (708)
Montana (292)
Nebraska (246)
Nevada (347)
New Hampshire (232)
New Jersey (612)
New Mexico (421)
New York (1,250)
North Carolina (1,169)
North Dakota (116)
Ohio (963)
Oklahoma (466)
Oregon (569)
Pennsylvania (1,035)
Rhode Island (123)
South Carolina (771)
South Dakota (234)
Tennessee (952)
Texas (2,836)
Utah (441)
Vermont (213)
Virginia (1,226)
Washington (656)
Washington, D.C. (115)
West Virginia (198)
Wisconsin (721)
Wyoming (287)

See More Accommodations...

See More Vacation Rentals...

Next keyboard_double_arrow_right

Bemuda Bay... Private bay beach. In unit laundry.

Saint Petersburg, Florida Vacation Rentals - 232.8 miles away

Tropical Gated 2bd/2ba condo, washer/dryer. Private bay beach, pools, etc. May-Dec 2022 - $2000/mo. Jan-April 2023 - $3500/mo. (already rented out) May-Dec 2023 - $2200/mo $150 cleaning fee, 13% t... » View Details

6 Reviews

From USD $2,000 per month

Additional Listings Within 250 miles of Islamorada

Exquisite Islamorada Townhome

Islamorada, Florida Vacation Rentals

This newly refurbished 2200 sq. ft. 2BR/2Bath luxury townhome with ocean views, has all the amenities: Pool, tennis,private beach and lagoon, and marina with 30ft boat slip.... » View Details

Contact For Rates & Specials!

Island Villa Properties

Islamorada, Florida Vacation Rentals

Patti Stanley’s Island Villa is your connection to finding inviting FL Keys vacation properties from Key Largo to Tavernier to Islamorada and beyond. Search "Island Villa Islamorada" and find us on th... » View Details

From USD $3,500 per week

Village at Hawks Cay Villas by KeysCaribbean

Duck Key, Florida Vacation Rentals - 14.2 miles away

Bedrooms: 2 Sleeps: 6 Bathrooms: 2

Stay at Hawks Cay with Huge Savings in the heart of the Florida Keys, the Village at Hawks Cay Villas offers an authentic island vacation, for romantic getaways, family reunions, destination weddings,... » View Details

From USD $199 per night

Key West, Rental by Owner in Truman Annex

Key West, Florida Vacation Rentals - 70.4 miles away

Bedrooms: 3 Sleeps: 6 Bathrooms: 3

Emma House can be rented in 2 ways. Emma House by itself is a 3 bedroom & 2.5 bath unit or Emma House with the Cottage creates a 4 bedroom and 3.5 bath retreat. It is deluxe unit with Tropical Keys St... » View Details

Contact For Rates & Specials!

Key West Hideaways

Key West, Florida Vacation Rentals - 70.9 miles away

Bedrooms: 2 Sleeps: 6 Bathrooms: 2

Experience the uniqueness of Key West by staying at one of Key West Hideaway’s one-of-a-kind vacation rentals. When you’re ready to escape the hustle and bustle of the “real world” why not enjoy the p... » View Details

From USD $188 per night

Island Wind Key West Vacation Home Rentals

Key West, Florida Vacation Rentals - 71.2 miles away

Bedrooms: 2 Sleeps: 5 Bathrooms: 2

Key West vacation home rentals in the heart of Old Town. 2 bed 2 bath conch home a block off Duval in Windward Park a gated community of 13 homes clustered around a 50 foot pool. Within walking dist... » View Details

From USD $175 per night

Lone Palm Old Town Key West Vacation Home Rental

Key West, Florida Vacation Rentals - 71.2 miles away

Bedrooms: 2 Sleeps: 6 Bathrooms: 2

Welcome to Paradise! Modern 2 bed 2 bath vacation home rental accommodations with a tropical flare. A block off Duval in Windward Park. 50 ft pool/BBQ/ hot tub. Walking distance to all the attraction... » View Details

From USD $2,500 per week

Key West Oasis 2 block walk to Duval Street

Key West, Florida Vacation Rentals - 71.3 miles away

Bedrooms: 1 Sleeps: 4 Bathrooms: 1

This Hidden Oasis is just a short 2 block walk to Duval street and all the action Key West has to offer. Fully equipped with everything you need to just RELAX. The Blender is waiting for your margar... » View Details

3 Reviews

From USD $195 per night

Rose Lane Villas

Key West, Florida Vacation Rentals - 71.6 miles away

Bedrooms: 1 Sleeps: 4 Bathrooms: 1

Rose Lane Villas is located in the heart of Old Town Key West, only half a block from Duval Street. These 1, 2 and 3 bedroom villas feature fully equipped kitchens, living rooms, complimentary parking... » View Details

From USD $249 per night

Key West Vacation Rental near Duval Street

Key West, Florida Vacation Rentals - 71.7 miles away

Bedrooms: 1 Sleeps: 4 Bathrooms: 1

A one bedroom, one bath home with pool only 2 blocks from Duval!... » View Details

From USD $188 per night

3 Room Art Deco Oceanfront Suite at Shelborne

Miami Beach, Florida Vacation Rentals - 73.7 miles away

Bedrooms: 3 Sleeps: 8 Bathrooms: 1

We are happy to offer you accommodation in Shelborne with 'the best location' next to Lincoln Road and only a couple of blocks to Ocean Drive in South Beach Miami Art Deco district that can create nic... » View Details

From USD $1,390 per week

Ocean Front Miami Beach Apartment

Miami Beach, Florida Vacation Rentals - 83.5 miles away

Bedrooms: 0 Sleeps: 4 Bathrooms: 1

Miami Beach/Sunny Isles Studio Apt - Ocean Front feet from the sand, furnished, util incld'd, w/parking, w/2 pools, gtd/sec . Absolutely beautiful... » View Details

From USD $1,150 per month

South Florida Kiteboarding School

Dania, Florida Vacation Rentals - 89.6 miles away

Bedrooms: 1 Sleeps: 2 Bathrooms: 1

Located in SE Florida, we offer boat-assisted lessons in waist deep water, kiteboarder-specific accommodations, Cable Park instruction, equipment sales and all inclusive packages.... » View Details

From USD $75 per night

Bahama Beach Club - Studios and 1/1 Apts

Fort Lauderdale, Florida Vacation Rentals - 91.5 miles away

Bedrooms: 1 Sleeps: 4 Bathrooms: 1

Enjoy clean, comfortable studio and 1/1 apartments in this nationally rated Superior Small Lodging just 2 blocks from the beach. Full kitchens, king beds, pool, laundry, BBQ, beach gear, free Wi-fi an... » View Details

6 Reviews

From USD $139 per night

Beautiful Townhouse At Downtown

FT.Lauderdale, Florida Vacation Rentals - 93.2 miles away

Bedrooms: 2 Sleeps: 6 Bathrooms: 3

Located in downtown Ft.Lauderdale, this beautiful brand new home is fully furnished, wood laminated floors, two spacious master bedrooms, two open balconies to enjoy the warmth of South Florida. close... » View Details

From USD $560 per week

Las Olas Art Deco House

Fort lauderdale, Florida Vacation Rentals - 93.6 miles away

Bedrooms: 6 Sleeps: 14 Bathrooms: 6

The house has 6 bedrooms, 7 bathrooms and a heated swimming pool. Located on the Intercostals with a jetski, 5 minutes from the beach. Weekly rates: $6,000-$10,000 Monthly rates: $20,000 - $15,000... » View Details

From USD $15,000 per night

Tranquil Tropical Guest House

Fort Lauderdale, Florida Vacation Rentals - 96.4 miles away

Bedrooms: 3 Sleeps: 6 Bathrooms: 2

Escape to our Relaxing Lush Tropical Oasis. Bungalow Six offers Luxurious Resort Bungalows. A Large Two Bedroom Home and a Smaller One Bedroom Bungalow share the property. Amenities: Salt Water Heated... » View Details

From USD $175 per night

Marco Island Waterfront Fun Anglers Cove Resort

Marco Island, Florida Vacation Rentals - 96.5 miles away

Bedrooms: 1 Sleeps: 4 Bathrooms: 1

Updated Marco River Waterfront Resort Condo. Elevator/ 2 Heated Pools and Spas/2 Tennis Cts, , Marina w/Boat Slips. Waterfront Tiki Restaurant Bar. Very Tropical! Marco Beaches 5 min. Golf & Naples 5t... » View Details

From USD $800 per week

Yacht and Beach Club - Waterfront Condo

Fort Lauderdale, Florida Vacation Rentals - 98.3 miles away

Bedrooms: 2 Sleeps: 4 Bathrooms: 2

Yacht & Beach Club condo is casual, tropical, carefully maintained and well suited for upscale business and vacation travelers (all apartments are two-bedroom/two bath). It offers a relaxing get-away ... » View Details

From USD $1,200 per week

Islamorada, Florida Vacation Rentals & Homes

Find a Islamorada, Florida vacation rental home for your vacation. Stay at one of our rustic Islamorada, Florida cabins, cozy cottages, or authentic condos. We have everything from large rental homes to small villas. Rent for a weekend, week, month, or entire season! Vacation rentals are great accommodations for families and large groups. Enjoy the convenience of a full kitchen and save money by eating in. Living like the locals at a vacation rental assures you an authentic travel experience. Browse our Islamorada, Florida vacation rentals and plan your vacation today!

Get Your Free RealAdventures Travel Newsletter

Subscribe to an inspiring travel newsletter full of great travel ideas, deals, destinations and adventures. Discover new places to explore, new adventures and new experiences.

Subscribe Today »

Add Your Travel Services and Accommodations

Add a multi-page listing promoting your accommodations, tours or travel services to customers on our network of travel sites. Your listing page includes an interactive map, availability calendar, reviews, photo-gallery and more.

Create Your Listing