Rentals in Islamorada, FL
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Search hundreds of Beachfront Vacation Rentals in Islamorada, Florida Keys
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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Islamorada, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.
Alligator Reef - Conch Home
Alligator Reef - Conch Home
Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean bre ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
75731 Overseas Highway
Gorgeous Key West Style 4 Bedroom Oceanfront Pool Home - 75731 Overseas Hwy.
Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and oth ....
4 Bedroom(s)
4 Bath(s) Vacation Rental
Islamorada, FL
Dream Escape at Anglers Reef in Islamorada
Dream Escape at Anglers Reef in Islamorada
2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An 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 terrace with barbe ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
132 Atlantic Lane
Beautifully Renovated 2 Bedroom Oceanfront Home - 132 Columbus
Looking for your next Home away from Home? You can not go wrong in this recently renovated 2 bedroom and 2 bath canal home in Lower Matecumbe at the 76 Mile Marker. This home has everything you need for your next get-away in Islamorada. Only one pr ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Islamorada, FL
La Jolla Resort
3 Bedroom Private Oceanfront House - Bahia
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overlooks the bay, with unparalleled privacy and nearly 2 acres of tropical trees, private boat docks and some of the best unobstructed ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL
San Roc
***Ocean Front, Pool, Spa, Dock, 2.5 Acres, Gated
San Roc is a beautiful 4 bedroom 3 bath home situated on over 2.5 acres with secluded woods. The Atlantic Ocean water views are spectacular. Located in Islamorada and the most sought after area known as "Millionaires Row" San Roc is a 2 level home. T ....
4 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
Bay Harbour D114
Stunning 3 Bedroom Condo with Oceanviews Located in Lower Matecumbe - Bay Harbour D114
Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does have Wi-Fi. The Bay Harbour Complex comes complete with two tennis courts, weight room, ....
3 Bedroom(s)
3 Bath(s) Apartment
Islamorada, FL
La Jolla Resort
3 Bedroom Private Oceanfront House - Sol
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overlooks the bay, with unparalleled privacy and nearly 2 acres of tropical trees, private boat docks and some of the best unobstructed ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL
Bay Harbour Condominium #204
??Luxury 3 Bedroom Condo -Amazing Views, Sunrise, Pool/Hot Tub, Kayak/Gym/Bikes
Located in Islamorada, Florida, this beautiful condominium is located in Lower Matecumbe Key, and feels like old Florida. Our home is a 3 bedroom, 2.5 bath and sleeps 6 people comfortably. The 3 bedroom unit includes an extra large living area and ba ....
3 Bedroom(s)
3 Bath(s) Condo - Sleeps 6
Islamorada, FL
Angler's Reef
Angler's Reef Resort Villa 136, a 2 Bedroom with Balcony Ocean View
The Angler's Reef Resort's villa 136 will provide your group with more than enough space to ensure their comfort and privacy. Complimentary covered parking will keep your mind at ease knowing your vehicle is well-protected. Just outside the living ar ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
113 Sunset Drive
Charming Beach Front Home in Lower Matecumbe - 113 Sunset Dr.
Near the house is the small Anne's Beach. There are nature trails, board walks to small lunch and BBQ areas, private sandy areas hidden in the mangroves and parking. The home is also near Robbie's Marina (where they feed the Tarpon), Bud n' Mary's Ma ....
4 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
Vacation Home
Islamorada Luxury Home deep water dock
Huge 40 foot swimming pool recently added. This is an incredible home featuring nothing but the best in high-end Florida Keys style décor and amenities. The location is spectacular with this home being just two minutes to either the ocean or bay. Pl ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL
102 Columbus
Charming 2 Bedroom Canalfront Home in Islamorada - 102 Columbus Dr.
Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Islamorada, FL
Vacation Home
Enjoy the lifestyle of the Key in Islamorada. Monthly rent have 32.5%discount
Very nice and clean Houseboat in the beautiful Islamorada in the 82 Mile The boat have one bedroom with a queen bed and a TV, another bedroom with a queen mattress, complete bathroom , kitchen, living room with TV also and a sofa bed queen, dining r ....
1 Bedroom(s)
1 Bath(s) Vacation Rental - Sleeps 4
Islamorada, FL
83003 Old Highway
Beautiful Oceanfront Oasis with Pool - 83003 Old Hwy.
Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in ....
4 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
Summer Sea Condominium
Kick Back In Islamorada!
Remodeled 2 Bedroom unit includes air conditioning, private balcony, cable TV, DVD player, full kitchen with cooking utensils, pots & pans, silverware, plates, glasses, microwave, coffee maker, dishwasher, iron, ironing board, blow dryer and refriger ....
2 Bedroom(s)
2 Bath(s) Condo - Sleeps 6
Islamorada, FL
4 BR Villa w/ pool Canal front-- Great access to the Ocean in Islamorada, Florida
4 BR Villa w/ pool Canal front-- Great access to the Ocean in Islamorada, Florida
MM 91. Situated on a clean, clear canal with deep water access to either the bay or ocean via Tavernier Creek! Enjoy your island time in this bright and breezy hideaway ... Two bedrooms/Two baths upstairs along with open living, dining and kitchen. T ....
4 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
Ocean Harbour M43
**Winter Promo** Luxurious Ocean View Condo w/Heated Pool & Jacuzzi
*** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large windows at this modern and luxurious oceanfront condo at mile marker 87. Accommodation - Sleeps 4 Master Bedroom: - King Size Bed - Nig ....
2 Bedroom(s)
2 Bath(s) Condo
Islamorada, FL
The Last Resort
Islamorada Oceanfront Estate | Pool, Beach & Dock | Next Availability Aug 2019
Islamorada Rental License: VR - 065 CHECK OUT A FEW WORDS FROM THE OWNERS BELOW INITIAL INFORMATION... 4 bed/5 bath beachfront on over 1 acre with a private beach, heated pool & dock Separate upstairs Den area sleeps up to 6 kids. * 7 Day minimum ....
4 Bedroom(s)
5 Bath(s) Vacation Rental - Sleeps 12
Islamorada, FL
Vacation Home
NEW RENTAL! Venetian Shores waterfront dream with pool and plenty of dockage.
This Venetian Shores pool home has 4,209 sq. ft. of living to spread out and enjoy your Keys vacation. This includes 2 living levels, with 2 bedrooms/1 bath on the first level and 3 bedrooms/2 baths on the second floor. Beautiful living room, update ....
5 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
122 Valencia Dr
Unique Venetian Shores Home with 3 Bedrooms and Dockage - 122 Valencia Dr.
Charming canalfront home in prestigous Venetian Shores. A simple yet lovely, ground level 3 bedroom, 2 bath home with direct access to ocean and bay via Snake Creek. With 70 feet of dockage, a fish cleaning station, gas grill, and great outside patio ....
3 Bedroom(s)
2 Bath(s) Apartment
Islamorada, FL
Vacation Home
2 BDR Penthouse-Breathtaking view-Designer Furnished-***7 Day Minimum Rental***
***NOTWITHSTANDING ANYTHING IN THE RATES PAGE THE MINIMUM RENTAL IS 7 DAYS***IF YOU SEARCH LESS THAN 7 DAYS MY PROPERTY DOES NOT APPEAR***THE MINIMUM RENTAL PERIOD IS 7 DAYS*** Bay Harbour www.bayinthekeyscom Luxuriously appointed condo located at M ....
2 Bedroom(s)
3 Bath(s) Condo
Islamorada, FL
91 West Plaza del Lago
Tastefully Renovated 3 Bedroom Canal Front in Port Antigua - 91 West Plaza Del Lago
Awesome renovated home in Port Antigua. The upstairs has 3 bedroooms and 2 baths. The kitchen has granite counter tops, stainless steel appliances, along with a serving window if you are out on the balcony. The downstairs has a great tv room with ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
Little Palm Caribbean Home
Little Palm Home - Enjoy Boat Harbor & Fishing Pier
Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone flooring. Open living and dining area all add to your tropical experience. Comfortable lounging chairs create a seamless trans ....
1 Bedroom(s)
1 Bath(s) Vacation Rental - Sleeps 4
Islamorada, FL
Angler's Reef
Oceanside Resort Home for the best getaway in luxurious Angler's Reef!
Our house is located in Islamorada, FL, the fishing capital of the world. Our single-family, Key-style home is located in an exclusive gated community of 50 island homes called Angler's Reef. The community includes a beautiful oceanfront pool, a priv ....
2 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 4
Islamorada, FL
The White Marlin Beach House
RATES REDUCED!! White Marlin Beach House, Islamorada
Contact owner for rates and availability at (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' Enjoy deep blue water or back country fishing. Dive, snorkel, and swim on a clear, white, sandy beach (rare in th ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 5
Islamorada, FL
Vacation Home
Bay Harbour - Developer Unit Every Upgrade Possible!!***7 DAY MINIMUM RENTAL***
***NOTWITHSTANDING ANYTHING IN THE RATES PAGE THE MINIMUM RENTAL IS 7 DAYS***IF YOU SEARCH LESS THAN 7 DAYS MY PROPERTY DOES NOT APPEAR***THE MINIMUM RENTAL PERIOD IS 7 DAYS*** Bay Harbour Luxuriously appointed condo located at Mile Marker 75 on t ....
3 Bedroom(s)
3 Bath(s) Condo - Sleeps 8
Islamorada, FL
Islamorada's Tropical Paradise
Tropical Paradise in Venetian Shores. Luxury Heated Pool / Spa, 4 Bikes & Kayak
Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled in 2014/15 so everything is tasteful, high quality, spotless and NEW!! HI SPEED WIFI and NetFlix is INCLUDED! A brand new luxury he ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL
Windy Cove #3
Great 3 Bedroom Oceanfront Town Home with Pool - Windy Cove #3
Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units ....
3 Bedroom(s)
2 Bath(s) Townhome
Islamorada, FL
Executive Bay - A5
Tropical getaway at Executive Bay, heated pool, fish off the dock, tennis
Relaxation at its best awaits you in our beautiful, Keys townhome on mile marker 87. Executive Bay Club is located in Islamorada, the Sports Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a h ....
2 Bedroom(s)
2 Bath(s) Townhome
Islamorada, FL
Islamorada Florida Keys Vacation Rentals, Hotels & Resorts
Plan your Islamorada Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Islamorada, Florida Keys.
Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Islamorada and the Florida Keys.
Spend quality time with your family and friends at cheap low rates you can afford, all while near the beach, nightlife, entertainment and a wide variety of beach activities. If you visit Key West in October, make sure to book your Vacation Rental here for Fantasy Fest. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.