58,368 properties available

Located in Summerland Key, Florida, United States. Little Torch Tropical Oasis April Available LITTLE TORCH TROPICAL OASISThis Beautiful Oasis is a recently renovated Manufactured Home on the corner of 2 Crystal Clear Swimming Canals. The backyard has a Sun Deck with custom Swim Ladder. Please note this is not a boating canal but you can swim, float or snorkel in your own back yard. This home has all the amenities you may need and more. It has a gas BBQ Grill. It's on a large fenced in lot with a nice shady area under Florida Native Gumbo Limbo Trees. Enjoy your own private spa on the large front deck. Wifi and Ethernet connection for Internet use included.This home is located about 30 minutes from Historic Key West where you can enjoy Shops, Restaurants and World Famous Entertainment. If you like Boating, Fishing and Snorkeling it is located in a great area minutes from the Ocean and about 6 miles by boat to the amazing Coral Reefs of Looe Key Sanctuary. This home is not on a boating canal but there is plenty of space for parking

Located in Cudjoe Key, Florida, United States. Casa Cudjoe: Tropical Canal Front Retreat on Cudjoe Key, Dockage, Boater's Paradise & Dog-Friendly! Welcome to Casa Cudjoe, a tropical haven nestled in the enchanting neighborhood of Cudjoe Gardens. This canal front retreat invites you to experience the epitome of Florida Keys living, with direct dockage granting you swift access to both the serene waters of the Atlantic and the boundless expanse of the Gulf. Gather your loved ones and unwind in the inviting embrace of the screened porch, where cherished moments and laughter unfold against the backdrop of passing boats. Sip on your favorite cocktail and revel in the tranquil rhythm of the waterways. Casa Cudjoe is your gateway to a world of leisure and adventure. Whether you're embarking on aquatic escapades or simply savoring the comforts of your home away from home, every moment is an opportunity to create cherished memories. While this tropical haven offers a wealth of delights on its premises, the allure of the Keys awaits your exp

Located in Cudjoe Key, Florida, United States. Cudjoe Cottages, swimming pool, just 20 miles from Key West House B - This lovely 3 bedroom 2 full bath home is located on the Atlantic Ocean. There is always a gentle breeze on the deck facing the ocean with a sunrise view. Comfortably sleeping six guest with dockage available.This property has a sunrise view, grassy yard for grilling. The kids and pets can swim and play all day. Boating, fishing and ocean snorkeling from the property. There also is a pool. All linens and dishes are provided along with washer and dryer.

Located in Summerland Key, Florida, United States. Canalfront house with private pool, WiFi, private washer/dryer, and central AC Skyway LivingOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'With three separate living areas and a private heated pool, this charming home is full of comfortable spaces for guests to enjoy. Stay in the main house, the downstairs lounge, or in the guest house complete with a full bathroom - each area has its own private entrance. But no matter where you decide to relax, there's room for you by the pool! Feel free to set up the private gas grill and enjoy a relaxing night near the canal. Inside, guests will be able to cool down in central air conditioning. Board games and a DVD player are on hand for relaxing evenings. The private washer/dryer will ensure you have everything you need for your days enjoying the sunshine.Things to KnowA futon in the downstairs area of the main house provides an extra sleeping space.The upsta

Located in Summerland Key, Florida, United States. Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapid Open Water Access! Introducing Casa Rosada, a delightful canal front haven nestled within the enchanting Cudjoe Gardens on Cudjoe Key. Offering an invitation to tropical relaxation, this charming abode provides a tranquil escape from the everyday. Dock your boat along the seawall and embark on fantastic fishing escapades in the pristine waters of the Atlantic or the Gulf, a mere stone's throw away. Rejuvenate with a refreshing dip in the inviting pool, cocktail in hand, as boats gracefully pass by, adding to the serene ambiance. While Casa Rosada offers a plethora of activities to enjoy, including its own array of offerings, if you're enticed to explore the wonders of the Keys, the vibrant allure of Key West awaits a convenient 30-minute journey, while the captivating charm of Marathon beckons within the same short span. Unveil the essence of island living at Casa Rosada!Please be aware of the following e

Located in Cudjoe Key, Florida, United States. Gorgeous New 4/3 With Heated Pool/Spa And Large Deep Water Boat Dock This is a beautiful newly built 4 bedroom, 3 bathroom house located on a cul-de-sac in quiet Cudjoe Gardens. The house includes a heated pool/jacuzzi, large 110 ft. dock with fish cleaning station and is equipped with water and electric, laundry room, and even an ice machine! The spacious Master Bedroom includes a walk-in shower, jacuzzi tub and easy access to the pool. Bedroom #2 has a queen bed and private bathroom. Guest bedroom #3 includes two twin beds. Guest Bedroom #4 has a king bed, spacious closet and direct access to the pool. The kitchen is fully equipped with a walk-in pantry and plenty of room for you to cook up the fresh catch of the day. For all you wine lovers there is a wine fridge/bar located adjacent to the kitchen. There is plenty of parking for boat trailers and extra vehicles. Just down the street is a marina with a boat ramp for your convenience. Whether you relax by the pool with a tropic

Located in Cudjoe Key, Florida, United States. Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West You're in the tropics... listen to the waves, rest, relax or fish, kayak and snorkel, if you wish to lose a few pounds. Three bedroom, two bath home, with direct ocean access, boat parking at the back door. Sunrise view, ocean breezes. Fully furnished, linens, cable/internet. This home is on a compound, we also have several one bedroom units as well as 2 bedroom. The perfect spot for large groups! Square Grouper restaurant and bar in the is down the street. Lower Keys Shuttle to Key West just steps from the home. Come and stay with us, you're sure to have a wonderful vacation.

Located in Summerland Key, Florida, United States. PEACEFUL PARADISE DEEP WATER CANAL 5 MINUTES TO OCEAN Fishing and Lobster season Location Location Location! Welcome to our very special community Summerland Key. WSummerland is one of the best fishing locations as well as being 25 minutes to the heart of Key West and 20 minutes to Marathon. Summerland is a quaint community of walkers, bicyclists and be it water enthusiasts…With 70 feet or sea wall you can certainly bring one or two boats with you. If you enjoy sunsets , peace and quiet along with beauty this is the place for you!Peaceful Paradise house is completely remoulded to give our guests a coastal elegance with a simplistic peaceful design. The open concept makes for a wonderful entertaining space for the family. Coffee and wine bar adds to the warmth of this extended kitchen and dining experience. If you’re looking to upscale your Florida Keys experience from one month or a few months you have found your destination.

Located in Summerland Key, Florida, United States. Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa Welcome to this Florida Keys gem, The Blue Pearl. The Blue Pearl is a beautiful, updated waterfront home with pool in a quiet neighborhood on Summerland Key (mile marker 24). Your stay here will relieve you of stress and warm your soul. The beautiful tropical landscaping provides privacy and a soothing atmosphere for your island adventures. It has a great location and convenient to world famous ocean and back country fishing and diving spots such as Looe Key, American Shoal (lighthouse built in 1880), Content, Marvin, Snipe, and Sawyer Keys, restaurants and shopping. Some of the best boating in the Key can be found on Summerland Key. Key West is only minutes away and offer endless entertainment, activity attractions, and dining options. It’s time for your tropical vacation and this house and upscale location will assure your needs are met. This wonderfully furnished waterfront home is available for monthly

Located in Summerland, California, United States. Pet friendly amazing location in paradise This home is located in Cudjoe Gardens one house in from the open water. Large open floor plan to kitchen with large center island and tons of storage equipped with almost anything a chef could need. 2200 sq ft split floorplan home. Brand new floors throughout. 3 bedrooms 2 kings, 1 queen, 1 queen sleeper sofa and 1 regular sofa. Two full bathrooms. Full house generator, pool, large PVC deck and dock. Marina with gas, bait, supplies and boat ramp only 1 block away. Very clean home with sunset view. Brand new AC.

Located in Summerland Key, Florida, United States. WEEKLY Oceanfront Home-Pool, Dock-Available Weekly or Monthly. Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,000 square foot custom built home set on over an acre of tropical landscaping with a sparkling new heated pool on beautiful Summerland Key in the Lower Florida Keys. This house is permitted for weekly or monthly rental.(Weekly rental permits are rare in the Florida Keys!) Enjoy watching sunrise views over the open water of the Florida Keys. Our Non-Smoking home, Seaclusion, is comfortable and beautifully furnished for your stay. This three bedroom, two bath, uniquely designed home offers elegant living spaces including a palatial living area with carpet and tiled floors, a kitchen with Bosch appliances, and an open staircase leading to the master suite. Relax and enjoy the luxury, space, comfort, and beauty of Seaclusion's wide open living space where you'll find "vacationing is easy." The master bedroom is located on the third floor. Thi

Located in Gulf Breeze, Florida, United States. Beautiful Renovated Studio Close to Pensacola Beach Enjoy Pensacola Beach in this beautiful studio apartment with your pup. Only three miles to the Gulf of Mexico. Fully equipped kitchen with granite countertops, solid wood cabinets, stainless steel appliances with ice maker. The bathroom has granite with solid wood vanity and a tiled shower. A sectional sofa and 50 inch Smart TV and WIFI will insure a relaxed stay. There is a small table for dining or use as a desk. The private fenced yard is perfect for relaxing and for you and your pup. There is a high quality queen air mattress ,in addition to the queen bed, if traveling with three or four people.

Located in Gulf Breeze, Florida, United States. Private Pool |Gulf Breeze Proper Home |Pet Friendly |Close to Pensacola Beach |King Master |Parking Welcome to Gulf Coast Paradise!In the heart of Gulf Breeze proper sits this amazing pool house with all of the amenities and feel of home. Bring the pets and enjoy being just a short 5-10 minute drive from gorgeous Pensacola Beach. Bring the boat and launch a half mile from the house at Shoreline Boat Ramp. There is plenty of driveway parking available for multiple vehicles and a boat trailer. The beautiful private pool is perfect for cooling off after long days at the beach. Inside, you'll find an open concept living room, kitchen, dining room, and breakfast nook. There is abundant natural light with views of the private back yard and pool. The kitchen has been completely updated with granite counters, stainless steel appliances, and new cabinets. It is fully equipped to handle all of your family's meals. The huge primary suite features a comfortable king bed and attached bath. Down the

Located in Gulf Breeze, Florida, United States. Single Family Home in Gulf Breeze Proper |Private Fenced Yard |Screened in Porch |Garage Parking Welcome to Gulf Breeze!Situated in the heart of Gulf Breeze, this home is just a short walk to Shoreline Park and Boat Ramp, and a quick drive over to the white sands of Pensacola Beach. This 4 bedroom single family home is a great option for your family's next trip to the Gulf Coast. There is room to spread out with over 1700 square feet and beds to comfortably accommodate 10. The split floor plan features a huge master suite on one end with access to the screened in porch, and 3 bedrooms on the other side with a large shared full bathroom. The spacious dining room and modernized, retro, fully equipped kitchen make family meals a breeze. The living room features floor to ceiling windows and a large smart TV. Outside you'll find a huge Florida room which is perfect for watching the kids play or catching up on a good book. The home sits on a large lot with a private, fully fenced back yard.

Located in Gulf Breeze, Florida, United States. BOOK 4 NIGHTS IN MARCH OR APRIL & GET THE 5TH NIGHT FREE! “You won’t find another place like this” The Salty Pelican is in an amazing quiet neighborhood with beautiful large trees, great paths for walking or taking a bike ride. You will love that you are just minutes to parks, the boat landing, Pensacola beach and our beautiful historical downtown Pensacola. After a fun day out, you can enjoy a private clean newly renovated home to call your own during your sunny Florida stay! The kitchen has top of the line appliances, great area in kitchen to have wine and laughs while preparing some of our Florida favorites. After dinner you will love the great entertainment room filled with games, and a large TV for movie nights. For your comfort each bedroom offers a queen-size bed and flat screen TV. Coming soon... outdoor patio area for relaxing and grilling! Professionally managed by Deja Blu Rentals...

Located in Gulf Breeze, Florida, United States. Dog-Friendly Home with Private Pool & High-Speed WiFi - Near Beach & Boat Launch Gulf Breeze ProperOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Full of comfortable corners inside and out, this home is ready to welcome groups and families ready to relax! The private pool at this home is perfect for cooling off on a sunny day, and the family dogs can enjoy the outdoor dog run. Enjoy fresh air in the screened-in porch, or enjoy central air conditioning inside the well-furnished living room.The desk workspace (which features a printer!) is perfect for people who need to finish up some remote work or schooling. The spacious kitchen includes full-size appliances, a prep island that doubles as a breakfast bar, and plenty of counter space for working away at your delicious projects. Helpful amenities like a private washer/dryer make this home an ideal family-friendly retreat on your next trip to Gulf Bre

Located in Gulf Breeze, Florida, United States. Great location and close to the beach and downtown! “You won’t find another place like this” The Fairpoint house is in an amazing quiet neighborhood with beautiful large trees, great paths for walking or taking a bike ride. You will love that you are just minutes to parks, the boat landing, Pensacola beach and our beautiful historical downtown Pensacola. After a fun day out, you can enjoy a private large home to call your own during your sunny Florida stay! The kitchen has all major appliances, great seating to have dinner or some wine and laughs while preparing some of our Florida favorites. After dinner you will love the great screened in patio room to kick back and relax.

Located in Gulf Breeze, Florida, United States. Luxe Private Beach Retreat Minutes to Pensacola! Discover the very best of Pensacola Beach from the comfort & convenience of this upgraded private retreat! Perfectly situated just minutes from the stunning turquoise waters of the Emerald Coast, enjoy relaxing beachside, the historic charm of Pensacola Village or the lively Pensacola Boardwalk simply a short drive away. Visit Navarre Beach, Fort Pickens, Opal Beach, Fort Walton, Destin, Perdido Key & more! The perfect place for family & friends, you will love this private oasis in Gulf Breeze!Recently upgraded and beautifully furnished throughout, this spacious and private four-bedroom home features an open floor plan with an upscale kitchen, counter-height seating, two dining areas, dedicated workspace, and a living room with 65” Smart TV.Fully appointed modern kitchen with stainless steel appliances, including stove, oven, refrigerator, dishwasher, and microwave. Bedrooms are comfortably furnished with fresh crisp new linens, pillows,

Located in Gulf Breeze, Florida, United States. Life's a Breeze! 🏖 Updated 3BR 5min to Pcola Beach Summary:Relax and Enjoy this charming, bright, spacious home in Gulf Breeze, Florida; the perfect vacation base for Pensacola area exploration! You'll have the entire home to yourselves: 3 bedrooms & 2 baths. The home can comfortably accommodate up to 8 adults. This is the perfect spot to access everything the area offers; near famous beaches, parks, shopping, & eating. It's sparkling clean and newly renovated! Perfect for families or friends who want all the amenities: where Life's a Breeze!The Space:Welcome to your Florida vacation destination! Only 2.5 MILES to the beautiful and famous PENSACOLA BEACH and 5 MILES to DOWNTOWN PENSACOLA!**Featuring NEW APPLIANCES, CABINETRY, FLOORING, and much more!This spacious home includes a large, airy Living Room, a bright Master Bedroom with a private en-suite Bath and two beautiful Guest Bedrooms with an additional Bath. It's a one-story home with hard floors throughout, making it very easy to

Located in Gulf Breeze, Florida, United States. Magnolia Breeze! Pet Friendly with Pool! Welcome to Magnolia Breeze! Located in a wonderful neighborhood in Gulf Breeze Proper. This large, cozy, family home is the perfect getaway with all the family including your fur friend. The open floor plan invites the whole family to gather for a meal and get cozy in the living room for movie night after a long day at the beach. The kitchen is fully stocked with all your kitchen essentials perfect for preparing any meals. The dining table can seat 8 comfortably and there is a breakfast bar with 4 bar stools. The master bedroom features a king sized bed with private access to the backyard. The master bathroom features a double vanity sink, a large, garden tub and walk in tiled shower. The guest rooms feature two twin beds and two queen beds. All guests room share a large bathroom with double vanity sink, large garden tub and walk in tiled shower. There is a large laundry room and full sized garage.This beautiful home offers a fenced in back yard

Located in Gulf Breeze, Florida, United States. ☀️Private Pool~Close to Beach~Sunroom~3BR You, Me, and the Sea Welcome to You, Me and The Sea: Welcome to You, Me and The Sea! Relax and unwind at this gorgeous, coastal home located in Gulf Breeze! This spacious home comes with a beautiful and well-equipped, full kitchen that will make preparing meals a snap! Offering a spacious king master suite with an en suite bathroom and two queen guest bedrooms with full bathroom in the hall for convenience, there's plenty of space for up to six guests. Head out to the backyard and cool off in your private pool or relax in the all-seasons furnished sun room where you can enjoy morning coffee or an evening cocktail. Fire up the grill for perfect summertime cookouts. With Pensacola Beach only a mere 3.8 miles away, you can take a walk on the world-famous white sand beaches and dip your toes in the crystal-clear emerald waters of the Gulf of Mexico! Come see why You, Me, and the Sea is sure to be your favorite vacation spot! * Amazing Private Pool

Located in Gulf Breeze, Florida, United States. Private guest apartment minutes from beach Private 1 bedroom, 1 full bath attached guest apartment in desirable Gulf Breeze proper. Sleeps 4 with queen sofa bed. Separate entrance, private parking. Fully stocked kitchen, washer/dryer, walk in closet. Safe neighborhood, police and fire station 2 blocks from the house. Boat/RV parking. Walking/biking distance to playgrounds, skate park, splash pad and tennis courts. 2 min drive to boat launch and dog park, 8 min to Pensacola Beach, and 10 min to historic downtown Pensacola. Pet friendly.

Located in Gulf Breeze, Florida, United States. Newly Remodeled Beautiful Beachfront Condo with Massive Balcony Regency Towers 703 West is a one bedroom, one bath condo on the 7th floor with a huge beach front balcony! Enjoy being steps from the soft sugar white sand and emerald green waters of the Gulf. This lovely property has tile flooring throughout and the furnishings are positioned to take full advantage of the beach views from the balcony. The bedroom has a king sized bed, a flatscreen tv and opens up to the expansive balcony. The fully equipped kitchen is updated with granite counter tops, stainless appliances and has an eat-in bar. Relax after a long day at the beach in front of the TV with a good movie or on the balcony listening to the waves. A stackable washer/dryer and WIFI complete this lovely condo. Make your next vacation memory at Regency Towers 703 West!Regency Towers is a gulf front complex with an East and a West tower. Surrounded by beach homes and low-density condos makes this complex a wonderful place to escap

Located in Pensacola Beach, Florida, United States. Pensacola Beach Resort Condo with Beach Access! Map out your Gulf Coast getaway to this top-notch 2-bedroom, 2.5-bathroom vacation rental located inside the pristine Portofino Island Resort! This family-oriented escape offers an updated interior, panoramic Gulf of Mexico views, cable TVs in each room, a private balcony, and access to all of the resort amenities (with an additional fee). Whether you're here to cast a line in the gulf, soak up the sun by one of the outdoor pools, or explore the island, this high-end resort condo has it all!-- THE PROPERTY --1,333 Sq Ft | Resort Amenities w/ Fee | Family Friendly | 180-Degree Gulf Views | Free WiFiDesigned for those looking to experience Pensacola Beach in style, this resort residence offers all the beach essentials, unbeatable views of the coast, and a prime location directly on the beach!Bedroom 1: King Bed | Bedroom 2: Queen Bed | Living Room: Queen Sleeper SofaPORTOFINO ISLAND RESORT (Addt'l Fees Paid on Arrival, Required): Outdoor po