Skip to content

Islamorada Vacation Rentals in the Florida Keys

Book Your Islamorada Vacation Rental Directly Online Here and Save!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Islamorada, Florida.

Vacation Rentals - Islamorada House

Beautiful centrally located home in the Florida keys.

Centrally located in the Florida keys close to Islamorada where there are great restaraunts and shops.Park your boat in your private dock with 35 feet of dockage.Minutes to the bay and very easy access to the ocean.There is access to a private homeowners beach with Cabañas and outdoor charcoal bbq.The home has 3 bedrooms and two bathrooms upstairs and one bedroom downstairs.There is a screened in patio where you can enjoy breakfast on the porch.......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Vacation Rentals - Islamorada House

Beautiful 2/2 Florida keys home rental

Beautiful 2/2 fully equipped Islamorda premier private neighborhood florida keys home . Private community with private beach , golf cart allowed on public road ,community access to private boat ramp. Will rent 3 month minimum to snowbirds From the month of November through April .Preferably to adults with no children and no pets. Access to 25' of rear dock space Beautiful views from terrace Please contact me for further details and informati.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Sandy Pointe Villa - Islamorada House

Beachfront Islamorada Villa with Dockage & Bay Views

The perfect Islamorada getaway awaits. Sandy Pointe Villa provides panoramic water views overlooking the Florida Bay, a private sandy beach and protected dockage, canal-side. This duplex features 3 bedrooms and 3 baths with an open layout for a spacious kitchen and dining room, and a living room with wall to wall sliding glass doors giving you unobstructed water views. Also on the main floor is two bedrooms, a comfortable master ensuite, an.......read more

3 Bedroom(s)
2 Bath(s) House Rentals

Vacation Home

Anglers Way Villa I - Islamorada House

End of Summer Paradise at Anglers Reef

2 Bed & 2.5 Bath Villa in Anglers Reef .Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious villa, one of the biggest 2 bedroom villas in the community. Cherry hardwood floors, kitchen granite counter tops, very spacious rooms, can accommodate up to 6. I.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Vacation Rentals - Islamorada Townhome

Beautiful townhome directly on the water

This stunning home is located at an exclusive sought out gated neighborhood in Islamorada, Florida. Located directly on the Bay with completely unobstructed views of the ocean. Home is meticulously decorates, with Beach House Chic decor. Home offers one master bedroom , second bedroom has two bunk beds , a loft that offers one queen size bed and pull out couch offers a full size bed in the living room. Two full baths one located one upstairs and .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 8 Townhome Rentals

Vacation Home

Islamorada Paradise! - Islamorada Townhome

Wake up in Paradise! Florida Keys - Islamorada (6 month minimum rental)

(6 month minimum rental) - $3,100 per month (without boat slip). Slip an additional $300 a month. Situated on a quiet street in Port Antigua, unwind in this fully renovated 3-story townhouse. The unique three story layout has a large entertainment living area with a half-bath, pool table, bar and living area and two terraces on the first floor, a spacious bedroom, full-bath, updated kitchen, living area, and large terrace overlooking the cove an.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 4 Townhome Rentals

Vacation Home

Vacation Rentals - Islamorada House

Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach

*****New Owners/Listing so you may not see reviews yet for that reason****** ***** Please email and I will answer any questions you have!***** Direct OCEANFRONT home with HEATED POOL, BOAT SLIP, & BEACHES in the desirable Anglers Reef Community. This 4 bedroom, 3 bath home has endless views of the ocean from every room. If you enjoy watching the sun rise, this home also features 800 sq ft of decking to enjoy the ocean views while sipping your .......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Summer Sea 320 - Islamorada Condo

Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada

Premier 1 bedroom unit with both that stunning bay view and a view of the pool off the balcony. Fully updated with the open concept kitchen open to the diving and living room. Stunning white cabinets and modern bathroom, Tile floors and granite countertops through out the apartment. Comfortable queen size bed with a pull out couch in the livingroom. The perfect place to lounge and enjoy your days! Summer Sea is a multi-story condominium on the.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Casa Dos Hondos - Islamorada House

Desirable Anglers Reef Villa (133) in Islamorada w/Optional On-Site Boat Slip

Welcome to paradise! "Casa Dos Hondos" is an immaculately clean, single family, Key West style home located in the desirable gated, resort community of Anglers Reef in Islamorada. The grounds, waterfront and amenities are spectacular, featuring a private heated pool on the coast of the Atlantic Ocean overlooking the Straits of Florida, two private beaches and a dedicated boat slip (available upon request)...all less than a 100-yard stroll from .......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Waterfront Wonder - Islamorada House

Opulent Waterfront Estate with Boat Dock, Pool, Hot Tub & Rooftop View - Dogs OK

Waterfront Wonder Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Swim right up to the edge of luxury at this ultra-private waterfront wonder. Located on one of the most prestigious streets in the Villages of Islamorada, this family-friendly property sits on a large deep-water lagoon with protected boat dockage. Enjoy immaculate indoor/outdoor entertaining .......read more

6 Bedroom(s)
6 Bath(s) - Sleeps 10 House Rentals

Vacation Home

The Palms of Islamorada - Islamorada Condo

Ocean & Bay Views. Welcome To Paradise!

Sleeps 4, 1 Bedroom - King Bed, 2 Full Bathrooms, Queen Sleeper Sofa, 2 TVs, Balcony, fully stocked kitchen, towels & linens provided, coin laundry available, elevators. Newly remodeled unit. Assigned, Covered Parking. Gated Community. Men’s & Women’s Fitness Centers, Club House, Pool & Jacuzzi, Ocean Front, Boat Ramp, Steps in to ocean. Great for Paddleboard & Kayaking. Walking distance to several restaurants. Minutes from several mar.......read more

1 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Scroll To Top