Vacation Rentals in Florida Keys

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Vacation Rentals in Florida Keys

Beba's Reef House

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Minimum Stay 1 Month. "Beba's Reef House" will capture your imagination the moment you enter the home and rise to…
  • from
  • $4500
    monthly

 

Atlantic Breeze- 3 Bedroom Family Vacation Home with Loft! Pet…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This home is great for families! It has been recently updated with new tile throughout, new furnishings and bedding, and…
  • from
  • $3700
    monthly

 

BARBADOS ISLE- 3 Bedroom Family Vacation Home with large deck…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Ready for some fun in the sun? This Ramrod Key vacation home is the perfect spot! This home is located…
  • from
  • $3000
    monthly

 

CASA TURQUESA- 3 Bedroom Oceanfront Family Vacation Home directly on…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water…
  • from
  • $6000
    monthly

 

Cruikshank- 3 Bedroom Oceanfront Vacation Home with Spacious Decks and…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Enjoy many peaceful days and evenings at Cruikshank Isle, situated right on the tip of Cruikshank Island on Summerland Key…
  • from
  • $4800
    monthly

 

Dolphin Beach- Luxury 3 Bedroom Oceanfront Family Vacation Beach House!…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Gorgeous luxury open oceanfront home on Summerland Beach. This expansive 3 bedroom, 2 bath home is just perfect for large…
  • from
  • $7000
    monthly

 

Fifty-Eight Palms- 2 Bedroom Waterfront Vacation Home with Large Heated…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • A tropical paradise awaits you at Fifty-Eight Palms. Located on Big Pine in the Port Pine Heights area. This vacation…
  • from
  • $3800
    monthly

 

Flying Could- 2 Bedroom Pet Friendly Vacation Home with Open…

  • 2 Bedrooms, 1 Bathroom, Sleeps 4
  • Fishing, swimming, boating.... Whatever your pleasure, the protective 75' seawall and clear, clean deepwater boating canal offers excellent choices! Relax…
  • from
  • $2750
    monthly

 

Lafitte Landing- Quaint 2 Bedroom Canal Front Vacation Rental Home…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Lafitte Landing is the perfect destination for your Florida Keys vacation. Very nicely appointed 2 bedroom, 2 bathroom canal front…
  • from
  • $2700
    monthly

 

Margarita Villa- 3 Bedroom Waterfront Pet Friendly Vacation Home -…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best…
  • from
  • $4500
    monthly

 

Owl's Nest- 3 Bedroom Bayview Vacation Home with Boat Dock!…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This tropical paradise is just waiting for you and your guests. Located near the end of a quiet lane this…
  • from
  • $3200
    monthly

 

Sunset Bay- Spacious Oceanfront 2 Bedroom Vacation Rental Home! Florida…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • This is a WEEKLY RENTAL! Welcome to Sunset Bay, where you’ll experience the most glorious sunsets! Located on tranquil Big…
  • from
  • $1750
    weekly

 

Tobago Hideaway- 3 Bedroom Pet Friendly Family Vacation Home! Florida…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Ready for that Florida Keys vacation? We are ready for you! Adorable ground level home with 3 bedrooms and 2…
  • from
  • $2300
    monthly

 

Spacious 3 Bedroom Pet Friendly Vacation Home with Boat Dock!…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Come and enjoy the wonderful Florida Keys lifestyle at Tropical Bay. Located at mile marker 22, close to Key West…
  • from
  • $2200
    monthly

 

Largo Kai

  • 5 Bedrooms, 6.1 Bathrooms, Sleeps 10
  • MINIMUM STAY: 28 DAYS Expansive ocean views are yours from almost every room in this magnificent ocean front home. This…
  • from
  • Contact Owner

 

Breeze Swept- Waterfront 3 Bedroom Vacation Home with Heated Pool!…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts décor…
  • from
  • $5600
    monthly

 

Bow Channel Manor - Oceanfront 3 Bedroom Family Vacation Home…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Welcome to Bow Channel Manor and step back in time to Old Florida! You'll find this plantation style home reminiscent…
  • from
  • $5200
    monthly

 

2 Bedroom Pet Friendly Vacation Home with Pool - Blue…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation…
  • from
  • $5600
    monthly

 

3 Bedroom Vacation Rental Home- Suncatcher's Dream Florida Keys

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Relax and enjoy this light and tropical, like-new vacation home with a private heated swimming pool. Step onto the large…
  • from
  • $4500
    monthly

 

Sunset Serenity

  • 3 Bedrooms, 3 Bathrooms, Sleeps 8
  • MINIMUM STAY: 29 DAYS. Enjoy the tranquil setting of this single family home located directly on the Florida Bay. Walk…
  • from
  • $5500
    monthly

 

Beacon Reef 306

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: 28 DAYS. Enjoy a relaxing summer and fall here in the Keys at this immaculate and charming two…
  • from
  • $4000
    monthly

 

The Palms #417

  • 1 Bedroom, 2 Bathrooms, Sleeps 2
  • Minimum Rental: 28 days. Everything in this unit is new - furnishings, linens, kitchen, appliances, and bath rooms. Great views…
  • from
  • $1800
    monthly

 

Boater's Delight

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM RENTAL: 29 DAYS. Beautifully furnished, this almost new single family stilt home sits on an ocean side canal front…
  • from
  • $3200
    monthly

 

The Palms 317

  • 1 Bedroom, 1.5 Bathrooms, Sleeps 2
  • Minimum Rental: LONG TERM RENTAL ONLY - 6 MONTHS MIN WITH 1 YEAR PREFERRED Completely furnished one bedroom condo with…
  • from
  • Contact Owner

 

Turtle Time

  • 3 Bedrooms, 2 Bathrooms, Sleeps 7
  • MINIMUM STAY: One Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home!…
  • from
  • $3800
    monthly

 

Summer Isle - 3 Bedroom Oceanfront Vacation Home with Private…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Surrounded by lush, tropical landscaping, this gated open-water vacation home comes equipped will all the thoughtful touches of home and…
  • from
  • $6900
    monthly

 

Sea Breeze - 3 Bedroom Vacation Home on the Canal…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Clean, sharp lines outline this welcoming vacation home located on a clean, clear deepwater canal. Easy access to some of…
  • from
  • $3100
    monthly

 

Quiet Waters - 3 Bedroom Family Vacation Home with Screened…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This Cudjoe Key home is neat as a pin. Brand new in 2007 with all the comforts of home. Bright…
  • from
  • $2400
    monthly

 

Romantic 2 Bedroom Pet Friendly Vacation Home with Boast Dock!…

  • 2 Bedrooms, 1 Bathroom, Sleeps 4
  • Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and…
  • from
  • $2000
    monthly

 

3 Bedroom Vacation Home on the Canal- Palm Villa in…

  • 2 Bedrooms, 2.5 Bathrooms, Sleeps 6
  • This beautiful custom home located in Jolly Rodger subdivision on Little Torch Key has the best of everything. Just furnished…
  • from
  • $5200
    monthly

 

LITTLE BAY - Lower Duplex

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 3 NIGHTS. This is one of three rental units on this fabulous property. The Little Bay property is…
  • from
  • $350
    nightly

 

LITTLE BAY - Upper Duplex

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 3 NIGHTS. This is one of three rental units on this fabulous property. The Little Bay property is…
  • from
  • $350
    nightly

 

BEACON REEF 501

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from…
  • from
  • $3200
    monthly

 

Our Island Thing - 4 Bedroom Family Vacation Home with…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This tropical paradise is just waiting for you and your guests. Located near the end of a quiet lane this…
  • from
  • $5000
    monthly

 

Ocean Magic- 5 Bedroom Beachfront Vacation Home with Private Pool…

  • 5 Bedrooms, 5 Bathrooms, Sleeps 10
  • A tranquil oasis is your destination at Ocean Magic, with tropical Caribbean waters right out your door. This estate quality…
  • from
  • $13500
    monthly

 

2 Bedroom Vacation Home - Mango House in Florida Keys

  • 2 Bedrooms, 1.5 Bathrooms, Sleeps 4
  • Simple and sweet with no muss, no fuss. It's all right here - Gulf Side! This quaint two bedroom vacation…
  • from
  • $1800
    monthly

 

Manatee Bay- 3 Bedroom Pet Friendly Family Vacation Home in…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Manatee Bay located in the Port Pine Height area is just the right spot to bring your family and friends…
  • from
  • $2500
    monthly

 

3 Bedroom Vacation Home with Private Pool- Keys Escape in…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 8
  • Escape from all your cares at this wonderful vacation rental on Cudjoe key. Just the spot to unwind and let…
  • from
  • $4500
    monthly

 

Island Time 1- Pet Friendly 2 Bedroom Vacation Rental in…

  • 2 Bedrooms, 1 Bathroom, Sleeps 4
  • Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge…
  • from
  • $2300
    monthly

 

Ibis Landing- 3 Bedroom Vacation Home with Open Decks and…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Ibis Landing is truly a remarkable property nestled by the Great White Heron Wildlife Refuge. Acres of nature's wonders can…
  • from
  • $3900
    monthly

 

Gulf Shores 3 Bedroom Family Vacation Home Florida Keys

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of…
  • from
  • $2700
    monthly

 

Galleon Bay- 2 Bedroom Pet Friendly Vacation Home in Florida…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Galleon Bay on Cudjoe Key is the perfect spot to enjoy your Florida Keys vacation. This home is centrally located…
  • from
  • $2500
    monthly

 

Egret's Landing - 3 Bedroom Waterfront Vacation Home with 40…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Welcome to Egret's Landing! From the private balcony located off the master bedroom living area, to airy and vaulted ceilings,…
  • from
  • $2900
    monthly

 

Cudjoe Ocean Shores - 3 Bedroom Pet Friendly Island Vacation…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Enjoy the rustle of swaying palms and the balmy tropical breezes from the screened and tiled balcony of this immaculate…
  • from
  • $2700
    monthly

 

2 Bedroom Waterfront Private Vacation Home- Cove Isle in Florida…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great…
  • from
  • $2800
    monthly

 

Coral House- 3 Bedroom Vacation Home with Private Hot Tub…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile…
  • from
  • $3000
    monthly

 

Cayo Villa- Luxury 3 Bedroom Family Vacation Home with Private…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 8
  • You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home…
  • from
  • $7500
    monthly

 

Casa Rosado - 3 Bedroom Dockside Tropical Vacation Home in…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This beautiful, vacation home is tropical, bright and confortable. You'll wish it was your own! Kitchen is fully equipped with…
  • from
  • $4800
    monthly

 

Sunshine Place

  • 1 Bedroom, 1.5 Bathrooms, Sleeps 2
  • MINIMUM STAY: 7 Days. You can have it all – privacy and convenience. The owners of this wonderful property called…
  • from
  • Contact Owner

 

BEACON REEF 314

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM RENTAL: 28 DAYS. Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in…
  • from
  • $3300
    monthly

 
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