Rentals in Florida Keys
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Cheap Hotels Florida Keys
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Summer get away desination- at the newly renovated three story fun house!
Key West Private vacation home
- 
5.0 Star Review
FRESH! FRESH! FRESH! Everything in this house is brand NEW and clean from linens, bed spreads, furniture, and the paint to name a few!
Looking for a vacation get away? A home away from home? This 1400 square foot, gorgeous water front stilt house gives you plenty of room to relax, have fun and most importantly right now social distance. N.......read more
3 Bedroom(s)
Sleeps 9
Private vacation home
Simonton Studio, an Old Town get-away for 2
Key West Apartment
- 4.9 Star Review
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
Rest-A-Shore ? Waterfront Home, Screened-in Private Pool, Near Sombrero Beach!
Marathon Private vacation home
- 4.7 Star Review
Rest-a-Shore is a modern home that is located on right on Sombrero Beach Road and a short bike ride along the beautifully paved and lighted road will take you to Sombrero Beach. This hidden gem is not only a beautiful beach it also has volleyball courts, gazebos, a playground, a fishing pier, restroom facilities, and hundreds of yards of white sand.......read more
2 Bedroom(s)
Sleeps 6
Private vacation home
Isabella on Paradise Place 2 bed 2 bath with Exotic Magnificent pool and Open
Marathon Private vacation home
- 5.0 Star Review
VACA-22-112
Isabella on Paradise place is a Picture perfect location in Paradise!!! The resort Pool is AMAZING! This property is located on Grassy Key with the most unique location. As you drive into the fully fenced yard you will find beautifully landscaped home with palm trees, a heated swimming pool with a paved deck, and barbeque grill.
2 Bedroom(s)
Sleeps 6
Private vacation home
FLAMINGO COTTAGE UNIT #1
Summerland Key Private vacation home
- 4.8 Star Review
The Flamingo Cottage comes with TV, AC & WIFI. UNIT #1 has full kitchen, and it's own private space. Enjoy the communal outdoor pool and covered patio that has a gas grill and picnic area.
Fishing adventures, bird watching, water sports or some down time relaxing in nature and the beauty of the most desired key in Florida. We’re twenty-fiv.......read more
Studio
Sleeps 4
Private vacation home
Duck Key Paradise Summer Discounts!!
Marathon Private vacation home
- 4.4 Star Review
Welcome to the historical Duck Key. What was once an exclusive island for the rich and famous, including President Truman, is now available to you. Canal Front property located in sought after area of Duck Key. This fabulous home is a 4 bedroom 2 bath. Sleeps 9
The stairs of the home are on the exterior providing complete privacy between the two.......read more
4 Bedroom(s)
Sleeps 9
Private vacation home
Canal-front home with private pool, dock, grill, & balcony - dog-friendly
Marathon Private vacation home
- 3.8 Star Review
Canalside Cabana
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
Find your sea legs and fill your days with Florida sunshine at this stilted, canal-side wonder! This spacious family home is amenity-rich, offering a private swimming pool, a dock, a.......read more
4 Bedroom(s)
Sleeps 10
Private vacation home
Honey Bun Hideaway by Brightwild | Pool & Grill!
Key West Apartment
- 4.3 Star Review
Summary:
Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old conch home is located in one of the most desirable areas, just steps away from the historic seaport and downtown. After a day of exploration, you can relax by taking a dip in the shared pool or enjoy a barbecue on the shared patio.......read more
Studio
Sleeps 2
Apartment
Spacious Good-Value Accommodation, Near Islamorada Brewery & Distillery
Islamorada Private vacation home
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more
Studio
Sleeps 4
Private vacation home
Pet Friendly Half-Duplex Cottage with kayaks and 40' Slip Option at Marina
Marathon Cottage
We have a lovely oceanside cottage in Marathon Key, Florida, close to everything with hidden amenities. The cottage has a large yard and plenty of room to park boats, RVs, and wave runners. This modernized cottage is for you if you all need a great place to stay. This quaint and cozy home offers good value and features new furniture and brand-new s.......read more
Studio
Sleeps 4
Cottage
Indulge in Home-Like Comfort! 3 Pet-friendly Units, Pool, Near Anne's Beach
Islamorada Private vacation home
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more
3 Bedroom(s)
Sleeps 12
Private vacation home
Caroline On My Mind-New Listing-Light, Bright and Airy!
Key West Condo
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings.
As you enter "Caroline on My Mind," you'll notice a stairway adorned with wainscoting, leading you to the entry. The ho.......read more
2 Bedroom(s)
Sleeps 4
Condo
Poolside Suite by Brightwild | Parking & Pool
Key West Apartment
- 4.8 Star Review
Summary:
Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the heart of Key West. The tropical themed home shares a pool and sun deck with Poolside Retreat which is located directly next door, ideal for groups looking to make new friends! Not to be left out, this property has a designated off .......read more
2 Bedroom(s)
Sleeps 6
Apartment
? Luxury house on the ocean with HOT TUB for 10 guests
Key Largo Private vacation home
- 5.0 Star Review
House on Key Largo paradise in the ocean. Perfect for big family . Enjoy a paradise on the water with a perfect view and location. Bring your boat and enjoy fishing. Rodriguez keys is near and waiting for our guests........read more
3 Bedroom(s)
Sleeps 10
Private vacation home
Easy access to the Ocean and Gulf
Big Pine Key Private vacation home
Leave your worries and enjoy the island life style. I promise you that this will be your favorite gateway. Beautiful sandbars, abundant wildlife. Don't forget the original delicious and key lime pie.........read more
2 Bedroom(s)
Sleeps 6
Private vacation home
Luxury Oceanfront 2BDR villa at private Sunset Key Island
Key West Private vacation home
Treat yourself to a dream vacation in our beachfront residence on the private island of Sunset Key, located in the middle of Key West Harbor. Our tastefully designed upscale villa has beautiful ocean views, a private pool, and a hot tub for our guests to enjoy. It boasts two spacious bedrooms, 2.5 bathrooms, a well-equipped chef's kitchen with a b.......read more
2 Bedroom(s)
Sleeps 6
Private vacation home
Pet-Friendly. LOCALS SAVE!
Key West Condo
- 4.8 Star Review
Steps away from Smather's Beach. This is a PET-FRIENDLY 3/2 unit in an exclusive gated community. Great location for a family or two couples - less than a hotel with all the amenities! Bring your own bicycles (or rent) to get around the island. The complex has 2 pools, 2 tennis courts, shuffleboard court, coin laundry and free parking for1 vehi.......read more
3 Bedroom(s)
Sleeps 6
Condo
Secluded beach hideaway with wide ocean views, kayaks & canoes
Key Largo Private vacation home
- 4.9 Star Review
Big View Hideaway
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
VACASA GUESTWORKS
This rental is operated and managed locally by an independent host.
Prior to your arrival, you will receive local host contact information, who will .......read more
2 Bedroom(s)
Sleeps 4
Private vacation home
Cozy Canal front apartment
Key Largo Apartment
*28 day minimum** Private 1 bedroom 1 bathroom apartment on beautiful canal. This cozy unit features a full kitchen, wireless internet, and cable TV. Patio overlooking a beautiful canal that leads out to open water. Shared small pool/spa and BBQ grill, in common area. Also shared use of paddle boards, kayaks, and bicycles. You can walk or ride bik.......read more
Studio
Sleeps 2
Apartment
3 x The Standard Double Queen Hearing Accessible at The Gates Hotel Key West
Key West Private vacation home
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few minutes’ walk to several local attractions. An onsite restaurant serves Latin-inspired tapas with local ingredients. The refreshing pool and pool bar are a relaxing spot to spend an afternoon in the sun. Hourly shuttle services ar.......read more
3 Bedroom(s)
Sleeps 12
Private vacation home
3 bedroom Gulfside Pool Home with Private Pool + 30' of Dockage
Marathon Private vacation home
- 5.0 Star Review
PAPAS PARADISE is located in the heart of the Florida Keys just minutes away from the open Gulf of Mexico at MM 52 in Marathon. This 3BR/3BA single family home is more than 1500 sq/ft and includes a large outdoor living area overlooking the beautiful canal and tropical poolside living area. In addition, the downstairs area is enclosed and screened .......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Spectacular Sunsets
Cudjoe Key Private vacation home
Escape completely in this open and airy 3 bedroom 2 bath oceanfront home, with a 10 x 14 ft pool. Situated on the northern shore of Sarcarma Bay on Cudjoe Key, this home offers tropical living and real southern exposure. The living area, the modern kitchen, and the master suite all open onto a full-length screened and covered porch overlooking the .......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Private Tropical Oasis
Islamorada Apartment
- 4.8 Star Review
Welcome to our Green Turtle!
My family and I relocated to the beautiful Florida Keys, from Orlando. The property we purchased has a 1 bedroom, 1 bath downstairs apartment. We are conveniently located within miles of restaurants, shopping, parks, beach, grocery stores and retail stores. We are on a private road, surrounded by conservation for to.......read more
Studio
Sleeps 2
Apartment
Luxurious Vacation! 3 Pools, Bar, Pet-friendly, Bike Rental!
Key West Private vacation home
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property.
PLEASE NOTE:
- The resort fee is not included in the d.......read more
Studio
Sleeps 2
Private vacation home
⚓ Beautiful Waterfront Vacation Home - Hook, Wine? & Sinker w/ Million ? Views
Marathon Private vacation home
- 4.8 Star Review
Ahoy Maties! Welcome to Hook, Wine & Sinker... this waterfront 3 Bedroom, 2 Bathroom vacation home is fit for every ocean loving pirate and mermaid alike. View the Sail Boats of Boot Key Harbor right from your waterfront, ocean side backyard. The views will truly impress your guests while they play cornhole, lounge poolside or soak in the relaxing.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Beautiful Home On The Bay
Tavernier Private vacation home
- 5.0 Star Review
Large Home on Florida Bay, wonderful sunsets, great fishing, diving, kayaking etc..
This home could accommodate two family with upstairs having four bedrooms and three baths and downstairs studio style living room with two bedrooms one bathroom, small kitchen. Large garage and utility room with extra shower.
Dockage accommodates protected .......read more
6 Bedroom(s)
Sleeps 14
Private vacation home
The Andros by Brightwild | 4th Floor Sunset View
Key West Condo
- 4.5 Star Review
Summary:
- Welcome to the quiet Sunrise Suites community located on the southeast side of Key West.
- Just 1 mile from the beach where aqua blue waters & loungers await.
- Only a 10 minute ride to downtown Duval Street restaurants, attractions & nightlife.
- The Great Exuma is a two bedroom two bathroom 4th floor condo with evening su.......read more
2 Bedroom(s)
Sleeps 6
Condo
Casa Margarita- 3 bedrooms | 3 baths | sleeps up to 8 | large heated pool & hot
Key West Private vacation home
- 4.8 Star Review
Casa Margarita is the perfect luxury retreat if you are looking for a peaceful place that also is in the heart of Old Town Key West. This three-bedroom, three-bath home features a large backyard with lush tropical landscaping, a heated pool, and a large hot tub with a capacity of up to six people. With a spacious covered patio, ample seating, and e.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
New to Vrbo SeaEsta! 1 Block to Sombero Beach! Bring your boat or rent ours!
Marathon Private vacation home
1 Block to Sombrero Beach, 70' waterfront w/ dockage. 3 Bedrms 3 baths. Large deck for cooking out. Direct access to the Atlantic. 65" TVs in all rooms. Enjoy your mornings by starting at our Coffee bar for Coffee, Cappuccino or a Latte. Everything you need is included with Sugar, coffee and creamers. Our home is fully furnished with all the essent.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Road's End by Brightwild | Steps to Duval St!
Key West Apartment
- 4.7 Star Review
Summary:
Just a stone's throw away from Mile Marker Zero lies the aptly named "Road's End," a charming 1 Bd, 1.5 Bth townhome located in the "Old Town Garden Villas" complex just a half block from Duval St. Spend time outdoors in the meticulously maintained courtyard that features lush landscaping and heated plunge pool. Whether you're looking f.......read more
Studio
Sleeps 4
Apartment
Modern Keys by Brightwild | Waterfront w/Dock
Key West Private vacation home
- 5.0 Star Review
Summary:
Welcome to Key Haven Estates! Located on the exclusive island of Key Haven, this gated community presents turquoise blue waters and luxury homes with a tropical touch.
Not far from the Key West beaches and downtown, an island escape awaits at Key Haven Estates. Stretching along the canal, the luxury homes are an opportunity to ex.......read more
4 Bedroom(s)
Sleeps 10
Private vacation home
Lo-Key 1: Discover Your Slice of Paradise, Charming Marathon Home, Pool, Deck, Patio & Dog-Friendly!
Marathon Private vacation home
- 4.7 Star Review
Escape to paradise at Lo-Key 1, a recently updated vacation home nestled in the heart of Marathon. This centrally located oasis invites you to bask in its incredible backyard. Take a refreshing dip in the inviting pool or unwind beneath the shade of the charming tiki bar after a day of exploring the enchanting Florida Keys. Marathon offers a multit.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Corner of Paradise in Key Largo
Key Largo Mobile home
- 4.0 Star Review
Calusa Campground Resort is a beautiful bayside property in W/ 24 hour security. This spacious park model trailer has one bedroom, fully equipped kitchen, full bathroom, and three sofa beds in the living room area. The enclosed patio is fully furnished for that afternoon cocktail. Outdoor barbecue, hibachi grill, and 1/2 bathroom for outdoor living.......read more
2 Bedroom(s)
Sleeps 6
Mobile home
Spacious Good-Value Accommodation! Courtyard View, Free Parking, Pets Allowed
Islamorada Private vacation home
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more
Studio
Sleeps 4
Private vacation home
**MODERN IN THE MEADOWS @ THE MEADOWS** Chic Private Home & Pool + LAST KEY SERV
Key West Private vacation home
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
MODERN IN THE MEADOWS proves you can blend modern and tropical styles into a beautifully laidback yet chic home. This fabulous monthly rental shines with its high-end upgrades, refined decor and upscale accommodations. Located in the qui.......read more
4 Bedroom(s)
Sleeps 10
Private vacation home
Key West Paradise!
Key West Private vacation home
Welcome to Paradise, stay at this beautiful key west home just 1 mile away from Duval st in a beautiful neighborhood and close to all local beaches! This Home has wonderful and spacious outdoor living space! Fully loaded with bikes to get you all over town!.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Islamorada Private vacation home
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-park.......read more
Studio
Sleeps 2
Private vacation home
Indoor / Outdoor Living in Old Key West
Key West Private vacation home
Our home is down a quiet lane in the heart of Key West.
Walk to Duval Street, organic “fast food,” yoga, beer, fishing, sunset sails, & good food. Your bikes & first beverage are ready for your arrival.
If you have questions or special requests, call for dates, stays, and arrangements.
We handle all needs directly & are avai.......read more
2 Bedroom(s)
Sleeps 6
Private vacation home
Pirate's Paradise 3 bedroom 2 bath
Little Torch Key Private vacation home
POOL COMING SOON!! Please note that this home is having a pool installed in 2023 for a completion date by January 2024. The rates for each month reflect possible construction and a finished pool by 2024. Pictures to come after completion!
Ahoy Matey! You have just dropped anchor at Pirate's Paradise! This jewel has open water views sitting direc.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Embrace Nature by the Ocean! Beach, Swimming Pool, Full Kitchen!
Islamorada Private vacation home
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more
2 Bedroom(s)
Sleeps 4
Private vacation home
High Tides and Good Vibes! 2 Relaxing Units, Pet-friendly Property, Pool
Islamorada Private vacation home
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more
2 Bedroom(s)
Sleeps 8
Private vacation home
Waterfront Penthouse sleeps 16 w/Pool & Boat Dock
Key West Condo
- 4.0 Star Review
Summary:
Gorgeous completely renovated 2400sqft waterfront Penthouse condo in downtown Key West. Boat slips available on-site with commercial ice machine, fish cleaning station and BBQ. Located in historic downtown Key West. 4B/4B with loft, sleeping 16. Less than 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: he.......read more
4 Bedroom(s)
Sleeps 16
Condo
Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi
Key largo Apartment
- 5.0 Star Review
Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do.
10 Min Drive to the Gilbert’s .......read more
Ocean View Splendor on Summerland Key
Summerland Key Private vacation home
- 5.0 Star Review
Enjoy the beautiful waterfront elevated home in the Florida Keys overlooking the Atlantic Ocean. Relax in the screened 25ft vaulted porch with gorgeous views and observe wildlife including the water birds and frequent dolphin visitors.
Inside is an open floor plan with 3 bedrooms and 3 baths including a master ensuite that faces the tranquil oc.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
One of the very few properties with a daily, weekly rental license in the Keys.
Summerland Key Private vacation home
- 4.4 Star Review
This is a newly remodeled four bedrooms elegant house. The property has its own private beach located in the heart of Summerland Key. It is the perfect Key for a vacation getaway. Summerland Key is an island in the lower Florida Keys about 20 miles east of Key West. The island has a private airport located 3 blocks from the house. The airport can b.......read more
4 Bedroom(s)
Sleeps 10
Private vacation home
Breezeswept Beach, Waterfront with pool
Ramrod Key Private vacation home
Located on the ocean side of Ramrod Key, this home offers open water sunrise views, a pool, a private sandy beach, and shallow lagoon access for kayaking and shallow boating. With the swimming pool, this home will be an excellent escape for those seeking a totally relaxed and quiet getaway. You will find everything you might need to make your time .......read more
2 Bedroom(s)
Sleeps 4
Private vacation home
Beach Adventure Awaits! Pool, Free Parking
Key Largo Hotel resort
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim in the tranquil waters. Try your hand with a stand-up paddleboard. Go snorkeling, kayaking, sailing, or more. With the beach and the bay as your front yard, it’s all right there for you. From water sports to beachside bars, from fi.......read more
Studio
Sleeps 4
Hotel resort
Enjoy Kew Wests Historic Old Town! 4 Spacious Units, Pet-friendly, Bike Rental!
Key West Private vacation home
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property. Each unit features 2 Queen beds and accommodates 4 guests. The p.......read more
4 Bedroom(s)
Sleeps 16
Private vacation home