Rentals in Islamorada, FL
Don't know Where To Stay? Select your destination and search for discount accommodations.
If you don't see your travel destination, just type it in the box and search for hundreds of Hotels, Resorts, Motels, Homes, Villas or Condos and more!
Cheap Hotels Islamorada, FL
Trying to save money on your vacation? VacationPlacesToStay.com has great deals and low prices on vacation rentals & hotels, Best Price Guaranteed.
Save when you book directly online for last minute deals with 3 to 5 Star Resorts, Inns, Hotels and more!
Search hundreds of Beachfront Vacation Rentals in Islamorada, Florida Keys
Book Your Vacation Homes Directly Online Here and Save!
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.
Little Bay Compound
A True Islamorada Oasis with Breathtaking Bay Views - Little Bay Compound
Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a ....
5 Bedroom(s)
6 Bath(s) Vacation Rental
Islamorada, FL
PARADISEPOINT
OceanfrontPeninsula Pool Dock water3sides 7nite min 6ppl max
MINIMUM stay 7 nights, MAXIMUM occupancy 6 people, rental pattern saturday to Saturday, SORY NO PETS COMMENTS AT HOMEAWAY #341722, VRBO #311382 A SLICE OF PARADISE. This is it...Search no More -you have found the needle in the hay stack. You are in ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
Islamorada Paradise
Islamorada Home In Paradise - NO HURRICANE DAMAGE TO HOUSE OR COMMUNITY
NO HURRICANE DAMAGE TO HOUSE OR COMMUNITY!!! This beautiful villa, 106 Anglers Reef, is fully licensed by the Village of Islamorada for Vacation Rentals, license # VR-224. It is located in the exclusive oceanfront gated community of Angler's Reef ....
2 Bedroom(s)
3 Bath(s) Villa - Sleeps 6
Islamorada, FL
Executive Bay Club
Executive Bay Club unit V4 Islamorada,FL
SERVICE ANIMALS are OK, otherwise NO PETS ALLOWED 30 Day Minimum Stays 2 Bedroom, 1.5 Bathroom townhome located in Islamorada, FL. Driving distance is only 90 minutes from Miami International Airport. Centrally located within the complex to tennis ....
2 Bedroom(s)
2 Bath(s) Condo - Sleeps 10
Islamorada, FL
Executive Bay - T2
**Winter Promo** Family Friendly Executive Bay Townhome with Beach & Pool
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions App ....
3 Bedroom(s)
2 Bath(s) Townhome
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
Windy Cove #1
Wonderful 3 Bedroom Oceanfront Townhome with Pool - Windy Cove #1
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
Paradise Cottage
RELAX in your PRIVATE Oceanfront Cottage!
1/1 cottage with breathtaking oceanfront views. Sleeps four comfortably. Private bedroom with queen bed. Living room has two full size futons. New kitchen with all stainless steel appliances. Very cozy and great views to enjoy in your dream vac ....
1 Bedroom(s)
1 Bath(s) Cottage - Sleeps 4
Islamorada, FL
Vacation Home
Top of the line Mobile home unit located at Islamorada resort. Full restaurant
Beautiful Mobile home fully loaded with all ameneties. breathtaking views just steps away from the Gulf of Mexico and the Atlantic Ocean. Unit will sleep 5 people comfortably. Queen bed in the rear bedroom plus two pull out beds in the main hall. Ev ....
1 Bedroom(s)
1 Bath(s) Mobile Home - Sleeps 5
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
ISLAMORADA PARADISE! Welcome to your private heaven on earth!
Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous panoramic ocean vi ....
3 Bedroom(s)
4 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
75130 Overseas Highway
Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy.
Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privac ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
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
Angler's Reef
Angler's Reef's Villa 119, a 2 Bedroom and 2.5 Bath Bungalow
Start your day with a refreshing plunge in the sparkling pool or an invigorating kayaking trip on the Atlantic Ocean. At Angler's Reef Villa 119 you can pamper yourself in the sun on the ocean front private beach while seagulls and pelicans grace the ....
3 Bedroom(s)
3 Bath(s) Townhome - Sleeps 6
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
Vacation Home
Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream
Welcome to Paradise! This fabulous Old Florida Style home with Tommy Bahama décor throughout is a Fisherman & Water Enthusiast's Dream! ***Ask about reduced seasonal rates Sept thru Nov! Located in a beautiful, quiet cul-de-sac, on a deep water ca ....
3 Bedroom(s)
4 Bath(s) Vacation Rental - Sleeps 10
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
Murphy’s Paradise
Fantastic Beachfront Home Private Gated 1 Acre Estate
Book now for your family vacation of a lifetime. Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of The Florida Keys. “The sport fishing capital of the world.� So beautiful that the Netflix series Bloodli ....
5 Bedroom(s)
4 Bath(s) Vacation Rental - Sleeps 12
Islamorada, FL
Vacation Home
Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.
Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and private dock, close to the best restaurants, and sight seeing. Peaceful, quiet and relaxing! Just what is needed to take your mind off ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
Vacation Home
Luxury Home Huge Pool & Dock Islamorada
Call us now for special discounts and also for rates not listed. Gorgeous three story home completely remodeled and refurnished using tropical island type colors and décor. Located on one of the only true deep water canals in Islamorada, this house ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
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
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
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
Vacation Home
Luxury Florida Keys Estate
Ocean Front, Lush Gardens, Private Beach, Deep-Water Dockage, Brand new Pool with Spa. This luxurious and newly renovated home is situated on the very desirable Lower Matecumbe Beach in Islamorada. This gated home offers supreme peace and privacy ov ....
3 Bedroom(s)
3 Bath(s) Large Estate Home - Sleeps 6
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
The Island Dog Villa
The World Famous Island Dog Villa of Islamorada in the Florida Keys
Perfect location for your Florida Keys Vacation Newly remodeled Villa in the beautiful Florida Keys. The Villa offers 2 Bedrooms, Boat Storage, Private Community Boat Ramp with Private Ocean Channel Access, Heated Pool, Private Community, LED Flat ....
2 Bedroom(s)
1 Bath(s) Villa - Sleeps 5
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
141 Ocean Lane
3 Bedroom Home with Ocean Views and Canal Dockage - 141 Ocean Ln.
"The Beach Fixes Everything".That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow resident ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
Bay Harbour A304
Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - Bay Harbour A304
Beautiful 3 bedroom and 2.5 luxury condo located at mile marker 74.5 bayside. This condo is nicely decorated and very spacious for you and your family. The unit has a great screened in porch off the living room. The complex has 2 tennis courts, wei ....
3 Bedroom(s)
3 Bath(s) Condo
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 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.