Vacation Rentals in Florida Keys

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Vacation Rentals in Florida Keys

4 Bedroom single family home with Private Pool - PLANTATION…

  • 4 Bedrooms, 3 Bathrooms, Sleeps 10
  • MINIMUM STAY: 29 DAYS Sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB,…
  • from
  • $6500
    monthly

 

Romantic 1 Bedroom Waterfront Vacation Home - Largo Kai Ground…

  • 1 Bedroom, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: 1 MONTH Only 1 - 4 people? Want something spacious but don't need a mansion? This is it!!…
  • from
  • $4950
    monthly

 

Oceanfront 2 bedroom Vacation Condo Rentals - The Palms #403

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: One Month This exceptional 2 bedroom and 2 bath condo is located in one of the most popular…
  • from
  • $2400
    monthly

 

2 Bedroom Single Family Vacation Home Rental - Villa Riolo

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in…
  • from
  • $3000
    monthly

 

Brand New Vacation Home for the Perfect Keys Vacation- Bayside…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 30 DAYS NEW HOME (2013) Spend the fall or winter in the Florida Keys! You will love this…
  • from
  • $3600
    monthly

 

Gorgeous 2 Bedroom Vacation Condo - Completely Remodeled- The Palms…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 30 DAYS A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been…
  • from
  • $2900
    monthly

 

Tavernier 3 Bedroom Canalfront Vacation Home with Heated Pool -…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 29 DAYS BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this…
  • from
  • $4200
    monthly

 

Casa Del Sol- 3 Bedroom Waterfront Vacation Home with Private…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Sit back and relax in this delightful home, situated on the open water. The entire rear wall of this home…
  • from
  • $5000
    monthly

 

Casa Caribe - 2 Bedroom Waterfront Vacation Home with Boat…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 7
  • This lovely 2 bedroom, 2 bath residence is located on Summerland Key at mile marker 24 just north of Key…
  • from
  • $2400
    monthly

 

Caribbean Dream- 4 Bedroom Waterfront Vacation Home - 3 Stories…

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. This beautiful home…
  • from
  • $5500
    monthly

 

Buttonwood - Pet Friendly 2 Bedroom Private Vacation Home with…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Just the right size at just the right price! Very comfortable and cute 2 bedroom, 2 bath home on Big…
  • from
  • $1800
    monthly

 

Breeze Swept- 3 Bedroom Oceanfront Vacation Home with Private heated…

  • 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

 

Blue Marlin- 3 Bedroom Waterfront Vacation Home with Boat Dock!…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 people in this…
  • from
  • $3500
    monthly

 

Blue Heron - Romantic 2 Bedroom Canal Front Vacation Home-…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation…
  • from
  • $2350
    monthly

 

Bay Pointe- Gated 3 Bedroom Family Vacation Home with Private…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 8
  • Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of…
  • from
  • $3800
    monthly

 

Barry Beach - 4 Bedroom Beachfront Family Vacation Home with…

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • This Florida Style home was built in 1965 and wonderful surprises await you on the inside. The ground level house…
  • from
  • $2750
    weekly

 

Atlantis - 3 Bedroom Vacation Home! Florida Keys

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Everyday is a great day at Atlantis. Beautiful Big Pine home located just minutes to Bogie Channel. This channel affords…
  • from
  • $2800
    monthly

 

Newly Remodeled 2 Bedroom Vacation Condo Rental -The Palms 402

  • 2 Bedrooms, 2 Bathrooms, Sleeps 5
  • MINIMUM STAY: One Month. Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You’ll love the uncluttered…
  • from
  • $2300
    monthly

 

Oceanview 2 bedroom Vacation Condo Rental - THE PALMS 506

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite condo complexes. This unit was recently…
  • from
  • $1900
    monthly

 

Pet Friendly Two Story 3 Bedroom End Unit Vacation Townhome…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 8
  • MINIMUM RENTAL: 3 NIGHTS. Villa Bella is a fabulous 3 BR/3 BA two-story townhouse. This end unit townhome “lives” on…
  • from
  • $250
    nightly

 

Oceanview 3 Bedroom Vacation Condo Rental - Private Balcony- The…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit…
  • from
  • $3700
    monthly

 

Angelfish Cove- 3 Bedroom Waterfront Vacation Home with Private Pool…

  • 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
  • Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of…
  • from
  • $3600
    monthly

 

Oceanfront 2 Bedroom Vacation Condo Rental - The Palms 301

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 28 DAYS. This exceptional condo has been impeccably maintained and is located in one of the finest condo…
  • from
  • $2100
    monthly

 

Quaint 2 Bedroom Vacation Cottage Rental - Sleeps 6- LITTLE…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 7 NIGHTS. This is one of three rental units on this property. The cottage is a ground level…
  • from
  • $2500
    weekly

 

Fabulous 3 Bedroom Vacation Beach House - SEA GRAPE

  • 3 Bedrooms, 2 Bathrooms, Sleeps 7
  • MINIMUM STAY: 28 DAYS FABULOUS BEACH HOUSE with sea grape trees on three sides and the ocean on the other!…
  • from
  • $6000
    monthly

 

Spacious 4 Bedroom Oceanfront Family Vacation Home- Largo Kai Upper…

  • 4 Bedrooms, 4.1 Bathrooms, Sleeps 8
  • MINIMUM STAY: 1 MONTH Looking for a spacious ocean front home but don't need a mansion? The upper two floors…
  • from
  • $9950
    monthly

 

Large 7 Bedroom Family Vacation Home with Water Views -…

  • 7 Bedrooms, 5 Bathrooms, Sleeps 24
  • This home is for the guests who expect extraordinary accommodations. Plan your dream vacation now to The Florida Keys and…
  • from
  • $18000
    monthly

 

Island Time 2 in Big Pine Key, Florida Keys Florida

  • 3 Bedrooms, 1 Bathroom, Sleeps 6
  • Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge…
  • from
  • $2500
    monthly

 

Comfortable 2 Bedroom Vacation Condo - Steps to Marina -…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM RENTAL: 27 NIGHTS (ONE MONTH). Comfortably furnished and ready for you. Conveniently located just steps from a full service…
  • from
  • $2000
    monthly

 

Private Five Star Luxury Vacation Home - 5 Bedrooms -…

  • 5 Bedrooms, 4.1 Bathrooms, Sleeps 12
  • Minimum Stay 29 days. This is the ultimate vacation home rental. If you are looking for a 5 Star Resort…
  • from
  • $30000
    monthly

 

Charming 2 bedroom, 2 bath home with an open living…

  • 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

 

Waterfront 5 Bedroom Family Vacation Home - Boat Dockage -…

  • 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
  • $14500
    monthly

 

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

 

Islamorada 1 Bedroom Bayfront Vacation Rental Condo - The Palms…

  • 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
  • $1900
    monthly

 
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