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Florida Keys: 412 properties found

A sun terrace, garden, and year-round outdoor swimming pool create a relaxing holiday retreat.
Limited-time Deal

Sweet Room

  • 1 extra-large double bed • Free cot always available
  • Breakfast included
    High-speed internet
    Only 4 rooms left at this price on our site
Per night
Original price US$917. Current price US$567.
3 nights, 2 adults

Earn 6% in Travel Credits on stays with the Genius Rewards Visa®

Plus get $150 in Credits after qualifying purchases on your card, an upgrade to Genius Level 3, and more. Terms apply.
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Banana Bay Resort & Marina
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This property spends a little extra to appear in this spot, and it matches your search criteria.
This property offers a year-round outdoor swimming pool, tennis court, and free use of bicycles.

Resort View Two Queens

  • 2 large double beds
  • Breakfast included
Per night
Price US$462
3 nights, 2 adults
This property offers a bar, barbecue facilities, and free on-site parking for ultimate convenience.

Economy Double Room

  • 1 large double bed
  • Only 1 room left at this price on our site
Per night
Price US$250
3 nights, 2 adults
An infinity swimming pool, fitness centre, and family-friendly restaurant create a perfect getaway experience.

King Room

  • 1 extra-large double bed
  • Breakfast included
    No prepayment needed – pay at the property
Per night
Price US$447
3 nights, 2 adults
A beachfront resort offering a private beach area, outdoor swimming pool, fitness centre, and restaurant.

Signature King

  • Entire studio1 bathroom301 ft²
    1 extra-large double bed
Per night
Price US$416
3 nights, 2 adults
This property boasts a fitness centre, year-round outdoor swimming pool, and a relaxing hot tub.

King Room with Sofa Bed and Balcony

  • 2 beds (1 extra-large double, 1 sofa bed)
  • Breakfast included
    High-speed internet
    No prepayment needed – pay at the property
Per night
Price US$507
3 nights, 2 adults
This beachfront resort offers a year-round outdoor swimming pool, fitness centre, and free bicycles.

King Room

  • 1 extra-large double bed
  • No prepayment needed – pay at the property
    Only 5 rooms left at this price on our site
Per night
Price US$874
3 nights, 2 adults
Offering a private beach area, beachfront access, and a stunning swimming pool with a view.
Late Escape Deal

King Room - Disability Access

  • 1 large double bed
  • Only 1 room left at this price on our site
Per night
Original price US$503. Current price US$352.
3 nights, 2 adults
Offering a private beach area, beachfront access, and a year-round outdoor swimming pool for relaxation.

Apartment with Pool View

  • Entire apartment1 bedroom1 living room1 bathroom1 kitchen732 ft²
    1 extra-large double bed
  • Only 1 left at this price on our site
Per night
Original price US$487. Current price US$444.
3 nights, 2 adults
A stunning swimming pool with a view complements family rooms and outdoor seating areas.

Standard Double

  • 2 double beds
Per night
Price US$299
3 nights, 2 adults
An inviting retreat with a private beach, infinity pool, fitness centre, and family-friendly amenities.

King Room

  • 1 extra-large double bed
  • No prepayment needed – pay at the property
    Only 5 rooms left at this price on our site
Per night
Price US$642
3 nights, 2 adults
This property boasts a private beach area, beachfront access, and a stunning swimming pool with a view.

Efficiency Queen Studio - Maximum 2 People

  • Entire studio1 bathroom248 ft²
    1 large double bed
  • Breakfast included
    Only 1 left at this price on our site
Per night
Original price US$564. Current price US$469.
3 nights, 2 adults
Beachfront property with outdoor swimming pool, bar, and free on-site private parking available.

King Room with Garden View - Non Smoking

  • 2 beds (1 extra-large double, 1 sofa bed)
  • Breakfast included
    High-speed internet
    Free cancellation
    No prepayment needed – pay at the property
    Only 4 rooms left at this price on our site
Per night
Price US$497
3 nights, 2 adults
A stunning swimming pool with a view, outdoor seating area, and barbecue facilities await guests.

Queen Room with Two Queen Beds - Non-Smoking

  • 2 large double beds
Per night
Price US$413
3 nights, 2 adults
Offering beachfront access, a year-round outdoor swimming pool, and free use of bicycles.

Guest room, 2 Queen

  • 2 large double beds
  • No prepayment needed – pay at the property
    Only 5 rooms left at this price on our site
Per night
Price US$486
3 nights, 2 adults
This property boasts a garden, terrace, and year-round outdoor swimming pool for ultimate relaxation.

Apartment

  • Entire apartment1 bedroom1 bathroom2,960 ft²
    1 large double bed
  • Only 2 left at this price on our site
Per night
Price US$324
3 nights, 2 adults
A vibrant hotel offering a year-round outdoor swimming pool, fitness centre, and free use of bicycles.

Standard King Room

  • 1 extra-large double bed
  • Breakfast included
    No prepayment needed – pay at the property
    Only 5 rooms left at this price on our site
Per night
Price US$507
3 nights, 2 adults

Hyatt Vacation Club at Windward Pointe
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Featured
This property matches your criteria and may be ranked higher in your search results. It will pay us a higher commission if you make a booking.
Offering sea views, air-conditioning, and a year-round outdoor swimming pool, this property delights.

Two-Bedroom Villa

  • Entire villa1 bedroom1 bathroom1 kitchen1,066 ft²
    3 beds (1 extra-large double, 1 sofa bed, 1 large double)
  • No prepayment needed – pay at the property
Per night
Price US$855
3 nights, 2 adults
This beachfront property boasts a private beach area, swimming pool with a view, and fitness centre.

Deluxe King Room Island View

  • 1 extra-large double bed
  • Only 1 room left at this price on our site
Per night
Price US$597
3 nights, 2 adults
Offering a private beach area, restaurant, bar, and year-round outdoor swimming pool for relaxation.

One-Bedroom Suite

  • 2 beds (1 sofa bed, 1 large double)
  • Only 5 left at this price on our site
Per night
Original price US$675. Current price US$487.
3 nights, 2 adults
A vibrant hotel offering a fitness centre, year-round outdoor swimming pool, and free airport shuttle service.

Queen Room with Two Queen Beds

  • 2 large double beds
  • Breakfast included
    High-speed internet
    Only 4 rooms left at this price on our site
Per night
Price US$577
3 nights, 2 adults

The Palms Hotel
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Featured
This property matches your criteria and may be ranked higher in your search results. It will pay us a higher commission if you make a booking.
Housed in a historic building, this property boasts a garden, bar, and year-round outdoor swimming pool.

Queen Room

  • 1 large double bed
  • Breakfast included
    Only 4 rooms left at this price on our site
Per night
Original price US$464. Current price US$424.
3 nights, 2 adults
Offering a sun terrace, garden, bar, and year-round outdoor swimming pool for ultimate relaxation.

Deluxe Queen Room - Disability Access

  • 1 large double bed
  • Breakfast included
    Only 1 room left at this price on our site
Per night
Original price US$673. Current price US$471.
3 nights, 2 adults
This luxurious resort offers a private beach area, spa facilities, and a stunning swimming pool.

Guest room, 2 Queen, No view

  • 2 large double beds
  • No prepayment needed – pay at the property
    Only 5 rooms left at this price on our site
Per night
Price US$1,104
3 nights, 2 adults

Blue Flamingo Resort Key West
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Featured
This property matches your criteria and may be ranked higher in your search results. It will pay us a higher commission if you make a booking.
This property boasts a year-round outdoor swimming pool, fitness centre, restaurant, bar, and sun terrace.

One Queen Bed

  • 1 large double bed
  • High-speed internet
    Only 1 room left at this price on our site
Per night
Original price US$537. Current price US$479.
3 nights, 2 adults
Offering a fitness centre, year-round outdoor swimming pool, and family-friendly restaurant for guests.

King Room with Sofa Bed

  • 2 beds (1 extra-large double, 1 sofa bed)
  • High-speed internet
    No prepayment needed – pay at the property
    Only 4 rooms left at this price on our site
Per night
Price US$512
3 nights, 2 adults