Lower Florida Keys Vacation Rentals
Vacation Rentals by Owner in Lower Keys .
We have partnered with a major provider for Vacation Rentals by Owner directly through . With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places to Rent in Lower Keys .
Search for Vacation Rental options here, then Book Securely on our partner site.
Your Condo by the Beach with Ocean View
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 privately owned condo facing the ocean with a view of swaying palms and turquoise waters. The Jungle Breeze condo is the perfect getaway for a romantic cou.......
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
DETAILS AND AMENITIES...
Enter this inviting open floor plan with incredible natural lighting throughout. Three sets of French doors take you from the living/kitchen space out to the outdoor entertainment area, consisting of a private heated lap pool all to yourself, propane gas grill, swing set, outdoor dining for 4, additional outdoor seating and pool loungers. Wood flooring, high ceilings and breezy ceiling fans in each room will keep you cool and refreshed on a sultry summer's day. Whip .......
10.0 Star Review
4 Bedrooms
- Sleeps 8
Key West Vacation Rental
Pets Allowed 
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Welcome to Bottom’s Up Bungalow — Your Private Tropical Escape in Old Town Key West
Step into a world of comfort and island charm at Bottom’s Up Bungalow, perfectly situated in the serene Meadows subdivision, just minutes from the vibrant heart of Key West. This immaculate 2-bedroom, 2-bathroom single-family home combines classic Florida bungalow appeal with modern amenities to create an inviting retreat that has earned over 100 glowing five-star reviews from delighted guests.
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
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" on 'More info on Brad & Dee' to learn more about island.
1800 Atlantic is located in the middle of the Island on the Atlantic side. Two miles u.......
Villa Fleur at Shipyard Condominiums
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 Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman's Little White house. Jus.......
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
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 why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West.
1/2 block to Hard Rock Cafe
Simonton Studio, an Old Town get-away for 2
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.
Located in a 6 unit compound this tiny Association is located in the heart of Old Town on Simonton St. Walk to the Hemmingway House, the Butterfly Conservatory and stroll Duval street with it's shops, restaurants, galleries and museu.......
Key West Rooster
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 Waterfront Park with water views and beautiful sunsets right from our porch. There are only a few homes in the Shipyard with a view like this! Most of th.......
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
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 and lush landscaping. A gas grill and outdoor furniture allow you to dine under the stars. Alternatively, enjoy dining in the open chef’s kitchen with.......
Peaceful Setting Amongst The Active Island Life Style
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 balcony is accessed from both the living area and master bedroom. The master bedroom has a king size bed, walk-in closet, and en suite bath. the guest b.......
Rare Penthouse 2 bed/2bath additional King in loft
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 of the Gulf of Mexico and the tarpon swimming below. This can be your place in the sun, a world of quiet pleasures and glorious sunsets, you'll revel.......
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always received great reviews on cleanliness. There will always be disinfectant wipes, liquid hand soap, dish detergent, laundry detergent, dishwasher tablets and a multitude of other cleaning supplies available for your use during your stay. It’s not just a place on the map, it’s a frame of mind, an At.......
Vacation Rentals by Owner in Lower Keys .
We have partnered with a major provider for Vacation Rentals by Owner directly through . With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places to Rent in Lower Keys .
Search for Vacation Rental options here, then Book Securely on our partner site.
Canal Front Paradise! Just a few yards from open water!
Welcome to paradise! Want to live like a local? Fish the reefs, snorkel Looe Key, dive for lobster, or kayak where dolphin and manatee play. Just navigate the few hundred feet of the canal to the open water of Pine Channel.
The house is itself is fully furnished with all the amenities. Central AC, ceiling fans throughout, dishwasher, washer/dryer, range, microwave, toaster, fridge, various coffee makers.
There is plenty of room for a boat trailer or RV in a side lot adjacent to t.......
10.0 Star Review
2 Bedrooms
- Sleeps 8
Big Pine Key Vacation Rental
Pets Allowed
Island Sunrise Resort- 3 acre estate with open water sunrises.
Island Sunrise Resort is a 3 acre open water estate. Enjoy the 250' long 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, The Sand Dollar House (sleeps 6). Large groups may rent the second house also. Keep in mind, if only one house is rented, the second one will re.......
Canal Front Home With Pool And Hot Tub
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 Harbor Channel. Less than a mile from the No Name Bridge, so there is access to fantastic fishing within walking distance even if you don't have a boat!.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Big Pine Key Vacation Rental
Pets Allowed
Manatee Watch | 5 bedrooms, pool, ocean access
Summary:
Gorgeous pool, big dock & easy ocean access from this 5 bed/4 bath home on Big Pine Key
The Space:
Discover your dream waterfront getaway on Big Pine Key! This impeccably updated 5-bedroom, 4-bathroom boating home offers unparalleled luxury and convenience, just seconds away from Pine Channel on the oceanside of Big Pine Key.
Nestled just four houses in from Pine Channel, this stunning property features a breathtaking custom pool and spa, perf.......
10.0 Star Review
5 Bedrooms
- Sleeps 12
Big Pine Key Vacation Rental
Pets Allowed
Lower Keys Retreat..... Come.... Relax in Paradise!!
This beautiful home located in Eden Pines, a Peaceful 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 and Chilled Pool, Newly remodeled bedrooms with new furniture...
A/C system updated... quiet comfortable..
The large living area is spacious and cheery with tall cathedral ceilings. The kitchen is perfect for the group to gather for imp.......
9.8 Star Review
3 Bedrooms
- Sleeps 8
Big Pine Key Vacation Rental
Pets Allowed
Paradise Retreat ~ BPK
~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 Marathon and other favorite "Burdines"
~Beautiful Winn Dixie grocery store on BPK
~28 day minimum rental for this property.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Big Pine Key Vacation Rental
Pets Allowed
Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
Cozy, clean, canal front home 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. Fully equipped kitchen with attached washer/dryer combo. Dining area (seating for 6) additional table for 4 on screened in porch. Additional amenities inclu.......
Awesome Open Water View at Blue Heron Estate
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, it is one of the best boating locations in the Lower Keys. With a 100' long dock adjacent to the property. Affordable pricing. The Blue Heron Estat.......
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 to Spanish Harbor Channel and easy access to the ocean or the gulf. Less than a mile from the No Name Bridge, so there is access to fantastic fishing within walking distance even if you don't have a boat!! The house is a short drive to Bahia Hond.......
9.6 Star Review
2 Bedrooms
- Sleeps 6
Big Pine Key Vacation Rental
Pets Allowed
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW
**** THE HOUSE IS NOW PAINTED WHITE, HAS A NEW FRESH LOOK**** 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. Boat Rental Available in town. We are looking for a seasonal renter but also consider month.......
\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"
-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.
-. Bahia Honda State Park with a beautiful beach.
-The Key where the deer live .
-Tiki bar to relax watching the canal.
-Full kitchen
-TV in every room.
-Directv and internet provider.......
10.0 Star Review
3 Bedrooms
- Sleeps 8
Big Pine Key Vacation Rental
Pets Allowed
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 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 snorkeling. The dock provides safe, secure and quick access to your boat. Launch or rent a boat at the 'No Name Bridge' and park it in the canal be.......
9.4 Star Review
2 Bedrooms
- Sleeps 6
Big Pine Key Vacation Rental
Pets Allowed
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 find in the lower keys. Nestled in the middle of the Key Deer Wildlife Refuge. This house is located 30 miles northeast of Key West. The property consists of three full lots at the tip of Doctor's Arm Peninsula. Please take a look at the aeri.......
10.0 Star Review
2 Bedrooms
- Sleeps 6
Big Pine Key Vacation Rental
Pets Allowed
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
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 beautiful tropical Florida Keys.
Peacefully rest each day in a spacious home with beautiful open living/dining room, vaulted ceiling, a large scree.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Big Pine Key Vacation Rental
Pets Allowed
SEA EVERYWHERE! Open Water & 2 Boat Basins!
Beautiful open-water views of the Bahia Honda bridge from nearly every room!
Key deer grazing daily in your yard.
Two boat basins capable of holding boats up to 30'.
Sunrises from your living room, sunsets from your dock.
Catch tarpon and snapper right off of the dock.
10 miles to Content Key. 3 miles to Spanish Harbor.
You are in the MIDDLE of the best place to catch tarpon, lobster, mahi, mutton, hogfish, mangrove, yellowtail, sailfish, wahoo, and blackfin tuna IN .......
4 Bedrooms
- Sleeps 9
Big Pine Key Vacation Rental
Pets Allowed
SEA FOREVER! Gorgeous Ocean-Front Paradise!
This feels like your own private resort. Two tiki huts cover lounge chairs and a 13-foot shuffleboard court. The pool and 24 palm trees frame the endless ocean views. Drive your boat straight out from the house to the #1 reef in North America! The Atlantic is 3 miles from your door. Enjoy the 1,500 Key Deer on the island, which will come right up to you without any worries. This truly is paradise found!.......
5 Bedrooms
- Sleeps 12
Big Pine Key Vacation Rental
Pets Allowed
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
Beautiful, newly redone 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 & enjoyment of many water sports and activities in the beautiful, tropical FL Keys. Kayaks, bikes, SU paddleboards available. Beach/National Seashore park just minutes away. Charters nearby to Looe Key Marine Sanctuary reefs for snorkeling o.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Big Pine Key Vacation Rental
Pets Allowed
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
Absolutely stunning, OCEANFRONT, dream home with panoramic views like none other. Truly one-of-a-kind property. Oceanfront POOL.
This brand new, beautiful 4 bedroom, 3.5 bath OCEANFRONT home is situated on a 3+ acre private peninsula in Big Pine Key offering 2,500+ square feet of spacious, new living space, plus an additional 800 sqft of covered oceanfront decks/porches/balconies.
Our dream kitchen features an 8-seat, 9’ x 5’ quartz island with ocean views abounding. Our great.......
Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friendly Accommodations!
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.
Discover the epitome of Keys living at "Rising Sun," a captivating waterfront home nestled on the serene shores of Big Pine Key!
This charming abode offers an authentic experience of the vibrant Keys Life, immersing you in the essence of island living. With a private boat dock along the seawall, you can effortlessly moor your vesse.......
10.0 Star Review
2 Bedrooms
- Sleeps 8
Big Pine Key Vacation Rental
Pets Allowed
Discounted July- ocean-ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
You have found it. So quiet. So peaceful. So beautiful. On Bogie Channel. One mile from No Name Pub. Only 30 miles from Key West! FUN IS EVERYWHERE. With ocean views from EVERY room in the home, this unique property boasts two completely separate units with an amazing one-bedroom, one-bath, and full kitchen, living, and dining area upstairs and a two-bedroom unit with a full bath, kitchen, living room, and dining area downstairs. There is plenty of outdoor space on your private oceanfront beach .......
10.0 Star Review
3 Bedrooms
- Sleeps 8
Big Pine Key Vacation Rental
Pets Allowed
Gorgeous Beachfront Home with a pool. Water views from every direction.
Step into your own island paradise! Welcome to this 5 bedroom 3 bath home. Featuring a large private beach with a heated pool. Plenty of privacy to relax wherever you at the home. Whether you are poolside enjoying the view, on one of three screened porches, or anywhere in the home, there is a water view. Go kayaking to the other islands or snorkeling right off your beach or watch the Sea turtles come ashore. Close to everything and just far enough away! A must for nature lovers! 2 King beds, 2 .......
10.0 Star Review
5 Bedrooms
- Sleeps 10
Big Pine Key Vacation Rental
Pets Allowed
Dates available Oct, Nov, Dec 2023
2/2Come and enjoy this newly renovated home. Be the first to enjoy! Located in one of the best fishing spots in the Florida keys, this canal home features a ramp for your small boat or jet ski. Relax among the Key Deer, enjoy the hot tub and fire pits. The home has a large covered patio and large covered fishing station. Washer and dryer in the garage. 2 deep freezers and an extra fridge for bait available in the garage for your usage. An ice maker is inside the home. Wonderful chef’s kitchen........
Private water front property with ocean access
Beautiful 15,000 sq ft water front property.
Steps away from the famous No Name Pub.
Steps away from the no name bridge which is great for fishing.
Also in walking distance from boat rentals and kayak rentals although we have kayaks to use at our place during your stay.
30 minutes from key west and 10 minutes to the beautiful beaches and Bahia Honda state park.
Also have over 30 ft of docking for your boat needs.
Great Location over all ! You will fall in love with ou.......
Upscale ocean front home & easy canal boat access to Gulf or Atlantic
THE ADVENTURER'S RETREAT - BIG PINE KEY BUNGALOW IS YOUR HOME AWAY FROM HOME WHERE YOU CAN RELAX AND ENJOY THE CENTRALIZED LOCATION TO ALL THE BEST ADVENTURES THE FLORIDA KEYS HAVE TO OFFER. ALL ROOMS HAVE AN OCEAN AND/OR CANAL VIEW!
-Location-
The Big Pine Key Bungalow is located on the East side of Big Pine Key. The living room and kitchen area opens up to three large sliding glass door windows giving an expansive view of the Bogie Chanel and No Name Key.
Within a 5 minute d.......