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.
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
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
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
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
454 Palm Drive LLC
Beautiful 3/3 Islamorada Waterfront Home
Our home is in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the southernmost island in Islamorada, at exactly Mile Marker 74, on the bayside. Our home is a 3/3, and can comfortably sleep six, ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
A8 Islamorada
Florida Keys' Jewel - Executive Bay Club
An ample 1,400 sq ft. town home in the heart of Islamorada. Two bedrooms and one bathroom upstairs. One bedroom has two queen beds and cable television. Second bedroom is set up with one queen bed and cable television. Sofabed and bathroom downstairs ....
2 Bedroom(s)
2 Bath(s) Townhome
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
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 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
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
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
Executive Bay - A7
**Winter Promo** Modern Executive Bay Club Condo with Pool & Beach
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
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
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
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'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
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
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
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
Executive Bay G5
Tastefully Renovated Townhome with Great Community Amenities - Executive Bay G5
This townhome at Executive Bay will sure make your home away from home! This unit has been completely renovated and decorated beautifully. This 2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and there is a bonus room off the Master ....
2 Bedroom(s)
3 Bath(s) Townhome
Islamorada, FL
ENTIRE BEACH HOUSE TWO IN ONE
W AVAILABLE BOAT Separate & Together Duplex 70' Concrete Dock w Private Beach
****************************************** Copy and paste the link below into a browser so you can see the 3D video tour of my amazing property ****************************************** https://my.matterport.com/show/?m=Cc7CWBsnjpA&brand=0 Enter ....
4 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 12
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
4BR Canal front home with splash pool, patios, boat slip & more!
4BR Canal front home with splash pool, patios, boat slip & more!
4BR Canal front home with splash pool, patios, boat slip & more! Seas the day is a fun, 4 bedroom house set on Lower Matecumbe Key in the beautiful Islamorada. On visiting the property, you'll first notice that it's just 3 small lots away from the At ....
4 Bedroom(s)
4 Bath(s) Vacation Rental
Islamorada, FL
121 Anglers Way, Islamorada FL
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef is a boutique complex of 52 home ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
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
Anglers Reef
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
This lovely oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500' of ....
2 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
Vacation Home
Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi
This tropical oasis includes a heated pool and dock that reaches out onto a protected lagoon that opens into the Florida Bay. There are 3 bedrooms and two bathrooms upstairs, and a downstairs bedroom suite with private bathroom that opens onto the po ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
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
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
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.