Lower Florida Keys Vacation Rentals
Book Places to Stay and Vacation Home Rentals in Lower Keys Directly Online Here and Save!
We have many choices for Lower Keys Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer for your visit to Florida.
Your Condo by the Beach with Ocean View
Key West Condo 
4.9
The Jungle Breeze condo at LaBrisa Condominiums.
*Ocean View
*Free WiFi
* Free Covered Parking
* Final cleaning included in price
* KING size bed.
* Accommodates 2 adults
* Recently renovated this condo features all new flooring and a brand new kitchen
* Full size washer and dryer.
This is not a hotel; it is a privat.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 2
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
Key West Private vacation home 5.0
PRESTIGIOUS TROPICAL RETREAT...
Indulge in this spectacular two-story home situated in the premier gated community of historic Truman Annex. Escape to a sun-kissed dream as soon you enter this picturesque community, surrounded by swaying palm trees inviting you to enter your island vacation home which is tucked away on a quiet lane. Totaling 4 b.......read more
4 Bedroom(s)
4 Bath(s) Sleeps 8
BOTTOMS UP BUNGALOW - 2 Bedroom / 2 Bathroom With PRIVATE POOL
Key West Private vacation home 5.0
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West.
This pristine Florida Bungalow is 2 bedrooms, 2 bathroom single family home and offers all the amenities you need to make this your perfect vacation. Including off-street parking, swimming pool, quaint gazebo equipped with wet bar and custom seating. Th.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
key west Condo 4.9
Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms, the kitchen and the living room. Birds of various types, boating activities, lush oasis gardens are just a few reasons why people keep returning to our paradise property. "Click" on 'more information' also "click" o.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Villa Fleur at Shipyard Condominiums
Key West Condo 4.9
Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and dining area. The living room features comfy furniture and a panel TV. One queen bedroom and one twin bedroom. Enjoy outdoor dining on the brick patio surrounded by a tropical landscape.
Villa Fleur is located in the Shipyard Co.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Key West Condo 4.9
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. This two bedroom Villa Vista is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.
The number one reason .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Simonton Studio, an Old Town get-away for 2
Key West Apartment 4.9
The Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everthing you need to fix your own cocktails and prepare some shrimp on the shared propane grill in the Courtyard.
Located in a .......read more
Studio
1 Bath(s) Sleeps 2
Key West Rooster
Key West Condo 4.9
Please call or text if you’d like to book our home
702 232... 3750
When booking our home please include a brief description of who you’ll be traveling with and what brings you to the area with your reservation request. We like to know who will be staying in our home ?
Welcome to your front row seat of the New Truman Waterfron.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Key West Private vacation home 4.8
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a private wonderland on the quieter end of Duval Street. Enjoy morning coffee or people watching on the elevated, partially covered front porch. The home’s backyard oasis includes a covered rear patio, a pool with waterfall feature an.......read more
5 Bedroom(s)
5 Bath(s) Sleeps 10
Peaceful Setting Amongst The Active Island Life Style
Key West Condo 4.8
Enjoy the New and Completely Renovated bathrooms to this tropical residence. This is quiet, peaceful living on the Atlantic Ocean. The spectacular view can be seen immediately upon entering the condo. The floor to ceiling glass walls provide a full sea panorama from the living room, dining room, kitchen and master bedroom. The 31 foot oceanfront ba.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Rare Penthouse 2 bed/2bath additional King in loft
Key West Condo 4.7
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath jacuzzi, have front row seats to the variegated lights of Mother Nature's Sunrises, have the convenience of a fully equipped kitchen, two sitting areas for extra comfort and flexibility and for countless hours to enjoy the views.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 8
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Key West Condo 5.0
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorated. Fresh paint throughout, all new hardwood flooring, new kitchen with granite counter tops, stainless steel appliances, and brand new designer furnishings make this a home away from home. A large rear courtyard with a wood sun d.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 5
Book Places to Stay and Vacation Home Rentals in Lower Keys Directly Online Here and Save!
We have many choices for Lower Keys Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer for your visit to Florida.
Canal Front Paradise!
Big Pine Key Private vacation home 5.0
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 on the porch, as the key deer meander out of the thickets in the early evening. Watch as a spectacula.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 8
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve
Big Pine Key Private vacation home 4.9
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. Great fishing and Diving. Bahia Honda Beach close by. Comfortably sleeps 6 plus two full sized sof.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Island Sunrise Resort- 3 acre estate with open water sunrises.
big pine key Private vacation home 5.0
Island Sunrise Resort is a 3 acre open water estate. Enjoy the 250' dock, pool, spectacular views of distant islands and the Old Bahia Honda railroad bridge during your stay at your own mini-resort. The Coral House (31463 featured house sleeps 8+) has a split floor plan with an eat-in kitchen and formal dining room. There is an additional 3/2 home,.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Airstream Glamping on the Ocean, MM 33 in the Fl Keys!
Big Pine Key Private vacation home
Luxury Airstream Travel Trailer fully equipped kitchen and bed linens. Book you stay and wake up to a water view every morning and sunsets by the canal every evening. Take advantage of the resorts large deck top pool, marina and boat docks. The general store is perfect for those last minute camping necessities........read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
Canal Front Home With Pool And Hot Tub
Big Pine Key Private vacation home 5.0
Terrific tropical getaway for rent!! 2 Bedroom 3 full bath canal front home with large in ground pool, hot tub and 60 feet of dock age! Located in desirable Doctor's Arm neighborhood, this house is located just steps from the famous No Name Pub on Big Pine Key. The boating cannel is just 200 yards to open water onto Bogie Channel and Spanish Har.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 6
Waterfront Big Pine Key Paradise
Big Pine Key Private vacation home 5.0
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 sits on a canal with easy access to the Gulf and Atlantic for some of the best fishing and lobster trapping in the world. The home is newly remodeled and high-te.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Gorgeous pool, 5 bedrooms, easy ocean access
Big Pine Key Private vacation home 5.0
Updated 5-bedroom, 3-bathroom boating home just four houses in from Pine Channel on the oceanside of Big Pine Key with gorgeous custom pool & spa. 60-foot concrete dock with large fender piles for your big boat. Convenient steps down into the deep water 70-foot wide canal so you can go for a swim or launch a kayak or paddleboard. Clear, deep cana.......read more
5 Bedroom(s)
3 Bath(s) Sleeps 12
Lower Keys Retreat.....
Big Pine Key Private vacation home 4.7
This beautiful home located in Eden Pines subdivision on Big Pine Key has the best of everything. Furnished with the finest tropical decor, flat screen TV's, wireless internet and roomy kitchen. Quiet setting, with landscaped yard & Heated Pool
The large living area is spacious and cheery with tall cathedral ceilings. The kitchen is perfect .......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Paradise Retreat ~ BPK
Big Pine Key Private vacation home 5.0
~3/2 home with heated pool located on large ,private and fenced property. Screened room and patio deck. Privacy is key to relaxation here on this property in Big Pine Key.
~Boat ramp within 1/4 mile with excellent access to Gulf~Atlantic
~Quick 20 minutes to our favorite "Square Grouper Restaurant", 45 minutes to Key West and 25 minutes to M.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Fisherman's Paradise/Easy Ocean Access/Quiet Key Deer Preserve! TIME TO FISH!
Big Pine Key Private vacation home 5.0
This cozy, clean, canal front home is located in a quiet, family friendly, National Key Deer Refuge. 3 bedroom, 2 baths with screened in porch, and plenty of outdoor living area underneath. Master bedroom with king bed with attached bathroom. One guest bedroom with queen bed, and the other with 2 twins, 2nd bathroom conveniently located inbetween........read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Awesome Open Water View at Blue Heron Estate
Big Pine Key Private vacation home 5.0
15 Acre Open Water Estate. Four bedrooms each with their own private bathroom. Large pool. Breathtaking views of the sunrise and historic Bahia Honda Bridge. Secluded location at the end of the road. Less than 2 miles to the Atlantic and around 3 miles to the Back Country. Check out the satellite view of the property and see for yourself. No doubt.......read more
4 Bedroom(s)
5 Bath(s) Sleeps 9
Heavenly Hideout, 2 Bedroom Canal Home in Eden Pines
Big Pine Key Private vacation home
Welcome to Heavenly Hideout!
YOUR FLORIDA KEYS CANAL FRONT HOME AWAITS...
NEW INGROUND POOL COMING BY DECEMBER 2023!!!
Vacation mode begins! Once you arrive at this lovely home, you'll be captured by the relaxing, fun outdoor space fully equipped with everything you'll want on vacation. Relax in one of the many seating areas downstairs or .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
2/2 Canal Front Home Big Pine Key. Easy ocean and gulf access!
Big Pine Key Private vacation home 4.9
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 to Spanish Harbor Channel and easy access to the ocean or the gulf. Less than a mile from the No .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Waterfront Big Pine Key Paradise
Big Pine Key Private vacation home 5.0
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 sits on a canal with easy access to the Gulf and Atlantic for some of the best fishing and lobs.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Doctors Arm waterfront with pool and Tiki hut. Ocean and backcountry access.
Big Pine Key Private vacation home 5.0
- Pool and Tiki hut.
-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. Size and number must be disclosed at booking. There are feeding and water bowls provided.
-Unsurpassed access to Gulf/back country an.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW
Big Pine Key Private vacation home 2.5
Florida Keys, Big Pine Key, located in Big Pine Key Florida. This home was remodeled in 2018 with new everything including a new AC unit. It's on a private canal on the bay side on Big Pine Key, in The Florida Keys, not far from Key West or Marathon Florida, close to shopping and still very private. Bring your boat there's plenty of dock space. Boa.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 6
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
Big Pine Key Private vacation home 5.0
-Remodeling house 3 bedroom and 3 bath.
-Please note that there is a 28 minimum rental period for this property.
- Dock and fish cleaning station.
-Excellent access to Atlantic and Gulf, minutes to the best lower keys fishing in country.
-Nice Jacuzzi to enjoy the sunset.
- 15 minutes from Bahia Honda State Park with a beautiful.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Big Pine Key! 3 bedroom house 2 bath sleeps 6
Big Pine Key Private vacation home
Large outdoor kitchen , sitting area, corn hole activity area, swim spa , entertainment ( outdoor tv & outdoor speakers, Hammocks for relaxation. Keywest is 28 miles from Big Pine. The house in a quiet neighborhood and close to groceries stores and local restaurants &bars. Water access is 0.3 miles for all your boating activities. Master bedroom.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm
Big Pine Key Private vacation home 4.6
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 Looe Key National Park, famous for it's crystal clear water, brilliant tropical fish and live coral is only 4 miles off Big PIne Key, great for diving or.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
Big Pine Key Private vacation home 4.9
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 find in the lower keys. Nestled in the middle of the Key Deer Wildlife Refuge. This house is.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
December 2023 Available!! Beautiful Canal Front Heated Pool 4 Bdr Home
Big Pine Key Private vacation home 5.0
Modern 3 bedroom 2 bath stilt home centrally located in Big Pine. Large heated swimming pool with tanning ledge. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store and Big Pine Park with tennis, basketball, skateboarding, racquetball, playground. Free public boat.......read more
4 Bedroom(s)
2 Bath(s) Sleeps 7
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
Big Pine Key Private vacation home 5.0
Searching for your own private Keys resort?
Look no further! Our "Retiro Sin Nombre" home is located on the famed and remote No Name Key.
This home offers a wonderful opportunity to enjoy the many nearby water sports, including abundant fishing and lobstering, diving, boating, kayaking and all the other outdoor activities in the beau.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Fishing, swimming and relaxing on the porch in Big Pine Key
Big Pine Key Private vacation home 5.0
Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Keys. Its located in Tropical Estates, a quiet upper scale community with water access throughout. A perfect location if you are looking for a tranquil island setting but close to the fun as Key West is just 25 miles south. This home has 3 large bedrooms, 2 with 1 queen bed, .......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Treehouse
Big Pine Key Private vacation home
Welcome to Barnacle Bed and Breakfast, your seaside sanctuary where luxury, comfort, and adventure blend perfectly. This beachfront retreat offers plush rooms with ocean views, a private beach, and exquisite breakfasts. For those seeking adventure, complimentary kayaks and bicycles are at your disposal. Here, you'll wake up to the sound of waves, s.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 2