Rentals in Florida Keys
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Eagles Nest
Eagles Nest- Corner canal front home with screened in balcony
The corner canal front home is located on Big Pine Key in the Fabulous Florida Keys. 3 bedroom 3 bath home with seawall and screened in porch. 3 bedroom/2 bath Canal Front Home on Big Pine Key with large sea wall and screened in porch. Boats are li ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Big Pine Escape in Doctors Arm
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm
The property has direct access to the Atlantic Ocean or the Gulf in minutes, providing some of the finest bluewater fishing coupled with backwater bonefish and permit fishing rivaled to none. The Loe Key National Park, famous for it's crystal clear ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
New Listing! Waterfront Gem w/ Pool & Boat Basin
New Listing! Waterfront Paradise w/ Pool, Boat Basin & Panoramic Ocean Views
** This brand-new listing may not have an abundance of guest reviews yet, but you can be assured of an exceptional stay. Thoroughly vetted, this home is professionally managed by TurnKey Vacation Rentals, two-time winner of the Travel Weekly Magellan ....
4 Bedroom(s)
4 Bath(s) Vacation Rental
Big Pine Key, FL
DEER HAVEN
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
Please note that we have a 28 day minimum rental period with no subletting. This is a Monroe County Regulation to preserve the beauty and peacefulness of Big Pine Key. PLEASE CLICK VIEW MORE BELOW TO VIEW CANCELLATION POLICY My property is a rare f ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Big Pine Key, FL
Waterfront Paradise
Waterfront Big Pine Key Paradise
House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6) Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the exclusive Doctors Arm area of Big Pine Key, in the lower keys, just 25-miles from Key West. This water front property s ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL
Tarpon Bay
Tarpon Bay/Big Pine Key Tropical and Fishermans Paradise
Please note that we have a minimum 28 day rental period. - Excellent access to Gulf and Atlantic fishing and diving waters - 60' dock to accommodate boaters - Tropical setting with several species of palms - Large covered outdoor deck - King size b ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Big Pine Key, FL
Florida Ocean Key
Florida Keys Pine Channel Water Front - Deep Canal
This concrete home is three doors down from the Pine Channel to the ocean. It’s located on one of the best deep water canal for great access to the Atlantic and/or back-country. This Lower Keys home has an open great room that includes the kitchen ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
The Blue Lagoon
The Blue Lagoon - A real cream puff!
Adorable vacation home in Port Pine Heights! Welcome to the Blue Lagoon . . . a beautiful, warm and inviting two bedroom, 2 bath coastal chic home in the ever popular Port Pine Heights. A quiet, serene setting with gorgeous sunset views from a full ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL
Lobstertail Lair
Big Pine 2/2 ,Water Views and Sunsets Located Oceanside Now rentting 20 seas
Nice Quiet 2 bedroom 2 bath beach cottage located oceanside of US 1 on a swimming canal next to open water canal. Sunset and open water view. Boat slip to open water next door by same owner. New Kitchen and all furnishings 2010. Close to all shoppin ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL
Time To Fish
Fisherman's Paradise in the Heart of Big Pine Key Deer Reserve
This waterfront vacation home is located in a quiet nature reserve, surrounded by several open undeveloped lots for extra privacy. 3 bedroom, 2 bath home with screen porch, and plenty of outdoor living area underneath. Master bedroom features king b ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Vacation Home
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - Boat lift , dock and fish cleaning station. -Excellent access to Atlantic and Gulf, minutes to the best lower keys fishing in coun ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Big Pine Key, FL
Vacation Home
Beautiful Trailer in Big Pine Key
Trailer in beautiful Big Pine Key with great fishing, breezes, and relaxation. Brand new with 2 bedrooms, 1.5 bath, kitchen and huge living room. jbwihbiwnciuncubdweuyfbcwey8acweiucniunuiewncaiuodbcuhabhuewbcienwCIUABWDCUYHNAEWU9CNAEIOUWNIPWNCUHEWNC ....
2 Bedroom(s)
2 Bath(s) Mobile Home
Big Pine Key, FL
Casa El Sueño
Canal Front Home in Big Pine Key
This two bedroom two bath home open floor concept is very comfortable. Master bedroom has sliding doors to screened in balcony that faces canal. Has a private bath and large closet. Additional room has two twin beds with very spacious walk in clos ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL
Vacation Home
Water Front Florida Keys Vacation Home
Quiet and comfy 3/2 water front home newly renovated. Enjoy all the wonderful amenities this home has to offer including fishing from your back yard or simply enjoying the view, ice maker for your freshly caught fish, BBQ grill, fish fryer, enjoy S'm ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Paradise at Key Deer Preserve
Big Pine Key, FL Waterfront 3 Bedroom 2 Bath Sleeps 8 people
Bring your Boat! This 3 bedroom 2 bath elevated home sits on Big Pine Key with the ocean in the front and a deep water canal equipped with Davits in back. This cozy home can sleep up to 8 people. Master Bedroom has a King Bed, First Bedroom has a ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL
Captain D's Hideout
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve
Beautiful, well maintained canal front home at the end of Big Pine Key. Surrounded by the Key Deer National Refuge. Wake up to Key Deer in your back yard. Only 30 miles from Key West and Duval Street. Concrete, step-down dock. Bring your boat. ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Doctor's Hideaway
Another day in paradise! Modern Keys home, with access to Gulf and Atlantic
-2017 construction home on a 10,000 sf lot on a 40 foot wide canal. -Please note that there is a 28 day minimum rental period for this property. - Pet friendly for your fur babies. No more then two and 15 lbs and less. There are feeding and water ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL
Vacation Home
Beautiful Sunsets- Waterfront Paradise
BEAUTIFUL SUNSETS & QUICK BOAT ACCESS to Pine Channel. Experience Breathtaking Sunsets View and Escape to Your Own Private Corner of Paradise... This Island style waterfront cottage is lushly landscaped with unobstructed water views it offers wonde ....
2 Bedroom(s)
1 Bath(s) Cottage - Sleeps 4
Big Pine Key, FL
Fisherman's Dream
Snow birds welcome! Great fishing
Luxurious home on deep canal with 100' of dock for your boats. A Fisherman's dream fish cleaning station. Close access to open water. Ocean view home in a quiet neighborhood. Close to marina and grocery shopping. Each bedroom has a private porch ....
4 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 12
Big Pine Key, FL
Palm Ave 3/3
Experience the Keys like a Local at this Spacious Canal Front Home with Dock!
This lovely waterfront home is located on mile marker 29, on the ocean side of Big Pine Key. Just 40 minutes from Key West, this hidden gem offers quiet relaxation, while still close enough to enjoy the party atmosphere of Key West! Dock your boat o ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Big Pine Key, FL
Big Pine Key Florida Keys Home
Florida Keys House, on canal, Key Deer, boating to Atlantic or Gulf
Very Comfortable, well furnished, 3 bedroom, 2 bath, stilt home. Large screened in porch facing east (cool in evening) overlooking canal and dock. Fully equipped kitchen with range, oven, microwave, dishwasher, pots pans, coffee makers, toasters. Was ....
4 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Buck's Beachhouse Bungalow
Great Family Retreat Property in Big Pine Key
Welcome to Buck's Beachhouse Bungalow . . . bring the whole family and enjoy the best of the Keys. A large gated, fenced property with lots of room for entertaining downstairs canal front. Great boating out to pine channel which is some of the best ....
4 Bedroom(s)
4 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL
Starfish Retreat
Your Paradise Retreat in the Lower Florida Keys
Starfish Retreat is your slice of Paradise located on Big Pine Key, only a 25 minute drive from Key West. This two story home comfortably accommodates 6 guests . It has spacious bedrooms and bathrooms. The common area, which includes living room, din ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Big Pine Oasis
Explore the Keys! Canal Front Property - Beautiful Sunsets
Conveniently located 10 miles from Bahia Honda State Park, 26 miles from Key West, 17 miles from Marathon, washer and dryer, dishwasher, microwave and oven/stove, direct tv, BBQ grill, outdoor shower, 2 car parking, in a quiet safe neighborhood. 52' ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL
Vacation Home
Perfect Keys Getaway
Beautifully furnished two bedroom two bath canal home located in Big Pine Key. Fully equipped kitchen with granite counters and stainless appliances, washer & dryer. Master bedroom with king bed, second bedroom has a queen size bed. Sofa in living ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Gulfside Getaway
Awesome boating from this 3/2 pool home on Big Pine Key
This well-maintained three-bedroom, two-bathroom tropical hideaway is just minutes from Pine Channel and some of the best boating in the Lower Keys! Located in the quiet neighborhood of Port Pine Heights on Big Pine Key, you can truly get away from i ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Big Pine Key House
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
Beautiful, new home directly on the water, perfect for boating with easy access to Atlantic or Gulf. Canalside docking for your boat. Amazing sunrises on the private porch deck. New furniture. This home offers a wonderful opportunity for relaxation ....
4 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Vacation Home
Gulf and Atlantic access fishing and diving paradiss
Large and comfortable home located on canal with direct Bluewater access 10 min to Atlatic. 3 spacious bedrooms, great sleeping setup for kids. 3 minutes to grocery and shopping in big pine including dive store and tackle shops. 25 minute drive to Ke ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL
Vacation Home
Welcome to Casa Del Mar
Welcome to "Casa Del Mar" a brand new mid-century modern home in Paradise! This home is a monthly vacation rental that must be rented for 28 days or greater. Quiet neighborhood , 3BR/2BA pool on deck. You can enjoy stunning oceanfront views from al ....
3 Bedroom(s)
2 Bath(s) Vacation Rental
Big Pine Key, FL
Bogie Cottage
Fabulous boating access on Big Pine Key
Great spot for boaters! Newly remodeled and nicely appointed 2 bedroom/2 bath home on Big Pine Key. The master bedroom has a queen-sized bed, en-suite bath and walk-in closet. The second bedroom has two twin beds and ample storage. There's cable TV a ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL
Tropical Beauty
Tropical Beauty 3 BR Retreat -Pool-Dock-Tiki Hut
Saturday - Saturday Rental This keys heated pool retreat is tucked away in a fantastic tropical paradise at Port Pine Heights, Big Pine Key. This lovely waterfront home has it all. This fantastic community is one of the most unique places in the wor ....
4 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Vacation Home
Open Water and Sunset Views Pool House in the Florida Keys
Newly renovated 4 bedroom 2 bath house on Big Pine Key. Property includes 35' dock, double lot, heated swimming pool, fire pit, BBQ, ice machine, downstairs storage, kayaks, paddleboards, cornhole boards and more! Master Bedroom upstairs with King ....
4 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL
~CASA AZUL~
~CASA AZUL~ Brand new construction, deep water canal with pool!!!
OPEN WATER VIEWS FROM ALL ANGLES AND BALCONIES! Meticulously designed Keys home with exquisite furnishings throughout home, quartz counter tops and top of the line stainless steel appliances. This brand-new home has a lovely open & entertaining feel ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 13
Big Pine Key, FL
Casa Del Mar
Welcome to Casa Del Mar
Welcome to "Casa Del Mar" a brand new mid-century modern home in Paradise! This home is a monthly vacation rental that must be rented for 28 days or greater. Quiet neighborhood , pool on deck. You can enjoy stunning oceanfront views from almost ever ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 12
Big Pine Key, FL
Nichols Key
Gorgeous 2 bedroom 2 bath canal front pool home
Gorgeous canal front 2 bedroom 2 bath pool home located on Big Pine Key. Excellent boating to the Gulf or the Atlantic with over 70' of concrete seawall. Mature landscaping surrounds the pool and tiki hut making it a tropical paradise The home featur ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Big Pine Key, FL
Reel NV
2/2 Canal Front Home Big Pine Key. Easy ocean and gulf access!
Terrific Key getaway for rent!! Newly remodeled 2 Bedroom 2 full bath canal front home with 50 feet of dock. Located in desirable Doctor's Arm neighborhood, this house is just around the corner from the famous No Name Pub on Big Pine Key. Quick idle ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Blue Heron Estate
Awesome Open Water View at Blue Heron Estate
Hurricane repairs are complete for the Blue Heron Estate. This is a 15 acre open water property with a 4 bedroom/4 bath house, a large pool and 70' of protected dockage. The grounds are a little rough but the views from the house of the open water an ....
4 Bedroom(s)
5 Bath(s) Vacation Rental - Sleeps 10
Big Pine Key, FL
Vacation Home
Mickey and Lynn's House of Windows
Secluded two story above garage corner lot gives you a panoramic views of water and near by park. Key deer frequent the property on this lovely sanctuary. Over a hundred feet of dock space and cleaning table. Secluded but convenient, located close ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Big Pine Key, FL
Keys Getaway
Beautiful Keys Getaway! Located on deep water canal for quick access to
This is a 2 bedroom, 2 bathroom concrete block house. It is located on a clean swimming canal right off Pine Channel. This Big Pine Key home has an open floor plan with updated kitchen, dinning room and living/TV room. The master bedroom has a Kin ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Vacation Home
Little Slice of Paradise
Newly remodeled 3 bedroom 2 bath in Big Pine Key. Perfect get away with everything you need for your home away from home. Spacious master bedroom with queen bed and private master bath. Second bedroom with queen bed and kids bunk bed room with twin ....
3 Bedroom(s)
2 Bath(s) Mobile Home - Sleeps 7
Big Pine Key, FL
Pine Channel Getaway
BIg Pine Key New House 75 ft dock 250 feet from open waters of Pine Channel
Welcome to our new spacious 3 bedroom 2 full bath home on a wide deep water canal with a 75 foot dock only 250 feet from the peaceful open waters of Pine Channel. Our comfortable 10 ft by 20 ft rear deck offers breath taking expansive views of the pe ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL
Vacation Home
Canal Front Paradise!
Welcome to paradise! Want to live like a local? Fish the reefs, snorkel Looe Key, dive for lobster, or kayak to the open water of Big Pine Channel, where dolphin and manatee play. Then return to your denizen and watch the boats turn for home. Relax o ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Skelley House
Skelley - Quiet Cottage on corner canal
This 3 bedroom 2 bath home located on Big Pine Key is perfect for your Florida Keys Get-A-Way. Tropical canal front resort style home. Enjoy a beautiful open living room and kitchen, large lanai area with views of the canal and tropical landscape. ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 7
Big Pine Key, FL
Big Pine Oasis
Explore the Keys! Canal Front Property - Beautiful Sunsets
Conveniently located 10 miles from Bahia Honda State Park, 26 miles from Key West, 17 miles from Marathon, washer and dryer, dishwasher, microwave and oven/stove, direct tv, BBQ grill, outdoor shower, 2 car parking, in a quiet safe neighborhood. 52' ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL
Reel Paradise
Reel Paradise - A Waterfront Boating Excape
Reel Paradise offer a large open format Keys retreat with vaulted ceilings, 3 bedrooms, 3 baths, dining room, large family room, sitting area, large screen plasma TV in the family room & private TV in each bedroom, 200 channel cable TV, DVD player, W ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Aqua Paradise Dream
Paradise in the Perfect Package
Beautifully decorated 3 bed/2 bath canal front home located in Big Pine Key. Master bedroom with queen bed and attached master bathroom. Newly renovated master bathroom has a walk in shower. Second guest bedroom has plush queen bed. Third guest bedro ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 10
Big Pine Key, FL
BP Pool Getaway
Tropical Waterfront Pool Getaway
This keys pool getaway is tucked away in a fantastic tropical paradise at Port Pine Heights, Big Pine Key. This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world. The gem like waters is the home ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
TROPICAL VACATION HIDEAWAY
Tropical Vacation Hideaway - Viisit Paradise
This waterfront stilt home is on a boating canal just five minutes at idle speed from Boggie Chanel, with imediate access to the Atlantic or the Gulf of Mexico. The home is decorated to give you a resort feeling, with tropical and nautical style d ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL
Sunrise on Tropical Bay
Recently remodeled 4 bedroom
Remodeled Ocean front with Boating and a POOL . This 4 bedroom, 3 1/2 bath, fully-furnished home is right on Bogie Channel on Big Pine Key. It has full ocean access and the time you spend exploring the Lower Key’s back country will be time you will ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL
Key Deer Hideaway
Fantastic boating home perfect for your Florida Keys getaway!
Spacious 3 bedroom/2 bath home with 50 feet of dockage in the heart of the Key Deer Refuge on Big Pine Key. Energy efficient and quiet, with vaulted ceilings and brand new furnishings throughout. Large, fully equipped kitchen with granite countertops ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 7
Big Pine Key, FL
Sandy Beach
Best Lower Keys Beachfront House and Dock on Florida Straits
Located directly on the Atlantic, this secluded home fronts one of the few natural sand beaches in the Florida Keys. The 165 foot long wooden dock has chickee for shade at the end. Sit and enjoy the sea breezes, watch the moon rise, or gaze out over ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Pelican Cove
Keys paradise hidden gem. Only 30 miles from Key West. Relax Relax Relax!
Located just 5 miles from Bahia Honda park rated top 5 beaches in the nation Located just 30 miles from famous Key West. Near Looe Key one of the worlds most beautiful snorling reefs. Enjoy the Key deer as they frequently come through this spacious s ....
3 Bedroom(s)
3 Bath(s) Mobile Home - Sleeps 6
Big Pine Key, FL
Catlin By The Sea
Catlin By The Sea Excellent Boating Location for Ocean and Back County Access
This canal front comfortable home is nestled in the North East Corner of Big Pine Key. Endangered Key Deer, found only in the keys, roam about the neighborhood as well as many other wildlife species. This property offers excellent boating with dire ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Vacation Home
Quaint Florida Keys home
We on Big Pine Key invite you to spend a little time with us and to experience the unique Florida Keys that is home to us. If total relaxation is your style then experience it keys style in the Lower Florida Keys. Walk through a nature trail with bir ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
South Seas Retreat
Family Friendly Home Nestled In A Quiet Subdivision.
This is a Family Home located in the Port Pine Heights Area of Big Pine Key which sustained no damage due to Hurricane Irma. The home is on a Canal with concrete seawall and davits. Minutes to the Back Country and minutes to the Ocean for GREAT FIS ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL
Tropical Caribbean Wonderland
Tropical Caribbean Wonderland
Note: This is a new unit the other RV from the reviews was damaged by Irma and this is the NEW replacement unit it is AWESOME..!!! We are located in a beautiful RV wooded park, with endangered Key Deer everywhere you look. We have a nice Pool and cl ....
2 Bedroom(s)
1 Bath(s) Recreational Vehicle - Sleeps 4
Big Pine Key, 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
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
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
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
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
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
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
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
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
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
100 Palo De Oro Drive
Beautiful Pool Home Located In Desirable Venetian Shores- 100 Palo De Oro
Looking for an amazing home in Venetian Shores? This home has everything - 4 bedroom, 4 bath home that has been updated. The kitchen is amazing, suited for any type of entertaining. The 3rd floor floor is a lofted master bedroom suite with a walk- ....
4 Bedroom(s)
4 Bath(s) Vacation Rental
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
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 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 - 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
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
2 bedroom 2 bath home in the HEART of Islamorada, Florida Keys-- walk festivals & more!
2 bedroom 2 bath home in the HEART of Islamorada, Florida Keys-- walk festivals & more!
Mile Marker 81. Cute and cozy two bedroom, two bathroom home located off the main streets, in the heart of Islamorada. A full porch wraps around the front and back yard, for relaxing and entertaining in the Florida Keys weather. Natural sunlight ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
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
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
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
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
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
Executive Bay - M3
**Winter Promo** Experience the Keys like a Local at Executive Bay - Townhouse 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 ....
2 Bedroom(s)
2 Bath(s) Townhome
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
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
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
Beach Dream House
Beach Dream House, relax and enjoy the clear waters of Islamorada FL
Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun rising over the Atlantic Ocean and superb views from every room in the house: 360 degrees of glass and a wraparound balcony . Pool and ....
3 Bedroom(s)
2 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
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
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
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
Angler's Reef Resort & Villas
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip
Beautiful 4 bedroom, 3.5 bath home for rent in Angler's Reef. This house has a bedroom with a queen bed and an ensuite bathroom downstairs. There is also a half-bath downstairs. The gourmet kitchen has marble counter tops, a wine cooler and a bar. Th ....
4 Bedroom(s)
4 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL
Find a Great Selection of Florida Keys & Key West Vacation Rentals
We have partnered with a major provider of vacation rentals, directly through FloridaKeysPlacesToStay.com. There are many apartments to choose from, and we now have the selection and value to offer our visitors going to Florida Keys FL.
book directly online to save! Choose from rentals with Wi-Fi, Pool, Oceanview, Beachfront and other amenities we have to offer for Florida Keys