Vacation Rentals with Hot Tub in Florida Keys

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Filtering by: Jacuzzi or hot tub

373 vacation rentals

(3) Very Good 

12

Conch Haven Old Town 1/1 MONTHLY Rental

Florida Keys / Key West

Key West apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$94

Price per night from

$94

(15) Excellent 

21

Islamorada Luxury Waterfront Condo with Boat Slip

Florida Keys / Islamorada

Islamorada apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Beautifully appointed, waterside condo!” This property is a beautiful, two bedroom condo, very well appointed, with everything we needed for a great stay! Islamorada is a great middle point to see the other parts of the Keys, and close to great restau
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Price per night from

$216

Price per night from

$216

(3) Excellent 

44

ADVENTURE AWAITS I - MARINER'S CLUB 606 - KEY LARGO RESORT STYLE VACATION HOME

Florida Keys / Key Largo

Key Largo townhouse

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$403

Price per night from

$403

(19) Excellent 

26

Spectacular Atlantic Ocean View Condo (MONTHLY)

Florida Keys / Key West

Key West apartment

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranqu
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Price per night from

$136

Price per night from

$136

19

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Florida Keys / Key West

Key West townhouse

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$299

Price per night from

$299

(1) Very Good 

11

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

Florida Keys / Cudjoe Key

Cudjoe Key cottage

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$149

Price per night from

$149

(13) Very Good 

32

75731 Overseas Highway

Florida Keys / Matecumbe Key

Matecumbe Key house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
“Relaxing!” The Florida Keys are so much fun and so very casual. The house was a great way to get our family together for a week and we all enjoyed ourselves, I could have stayed for a month. The guys all went fishing and the rest of us floated in the
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Price per night from

$1,045

Price per night from

$1,045

38

Paradise on the water

Florida Keys / Key Largo

Key Largo house

4 8 28 nights min

  • 4 bedrooms
  • sleeps 8
  • 28 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$252

Responds fast!
avg. 1 hour 9 minutes

Price per night from

$252

(4) Excellent 

48

Key West Condo close to the Ocean

Florida Keys / Key West

Key West condo

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$260

Responds fast!
avg. 1 hour 48 minutes

Price per night from

$260

(4) Excellent 

31

Duck Key Paradise

Florida Keys / Duck Key

Duck Key house

3 9 28 nights min

  • 3 bedrooms
  • sleeps 9
  • 28 nights min
  • Nearest beach 19 mi
  • Swimming pool
  • Child Friendly

Price per night from

$331

Responds fast!
avg. 13 minutes

Price per night from

$331

(85) Very Good 

26

Tropical Escape

Florida Keys / Key West

Key West apartment

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Very comfortable and all around great place to stay.” It was very clean, comfortable and homey. The pool was great and it's very close to Key West and a beach. We really enjoyed our stay. Provided plenty of towels, pool accessories, kitchenware, etc.
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Price per night from

$222

Price per night from

$222

(40) Excellent 

39

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Florida Keys / Key West

Key West apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with cha
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Price per night from

$352

Responds fast!
avg. 2 hours 6 minutes

Price per night from

$352

(4) Excellent 

22

Key West Florida Beachfront Condo

Florida Keys / Key West

Key West condo

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks
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Price per night from

$302

Price per night from

$302

26

Bay Harbour D114

Florida Keys / Long Key

Long Key house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$323

Price per night from

$323

40

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Florida Keys / Islamorada

Islamorada condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$172

Price per night from

$172

42

NEW LISTING! Oceanfront home with private hot tub and amazing ocean views!

Florida Keys / Conch Key

Conch Key house

4 10 28 nights min

  • 4 bedrooms
  • sleeps 10
  • 28 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$216

Price per night from

$216

38

Shark Key Home with beach 10 Min from Duval St

Florida Keys / Key West

Key West house

3 8 21 nights min

  • 3 bedrooms
  • sleeps 8
  • 21 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$292

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$292

(2) Very Good 

15

Island Living

Lower Keys / Summerland Key

Summerland Key house

3 8 28 nights min

  • 3 bedrooms
  • sleeps 8
  • 28 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

Price per night from

$227

Price per night from

$227

(19) Very Good 

18

Gorgeous Spa Villa, Marina in Florida Keys

Florida Keys / Duck Key

Duck Key villa

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Loved it” Just got back from staying in this Villa. We were very happy with everything. The villa was clean & beautifully decorated & the location was perfect. I have stayed in Hawks Cays Villas twice before & this was the nicest. We will stay here
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Price per night from

$175

Responds fast!
avg. 3 hours 56 minutes

Price per night from

$175

(1) Very Good 

70

Mediterranean styling, oceanview, pool, dockage, hot tub

Florida Keys / Marathon

Marathon house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$500

Price per night from

$500

(12) Very Good 

47

Private Beachfront Paradise

Florida Keys / Matecumbe Key

Matecumbe Key house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Nicest rental property we have ever stayed in!!” Beautiful home on spotless white beach! Property has been updated with upscale furnishings throughout. Granite, leather furniture, redone bathrooms. Well stocked for all your vacation needs -- towels
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Price per night from

$504

Price per night from

$504

(2) Excellent 

25

KEY LARGO YACHT CLUB 8

Florida Keys / Key Largo

Key Largo apartment

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$141

Price per night from

$141

(2) Excellent 

17

Incredible Luxury Home with Waterfront!! Paradise

Florida Keys / Islamorada

Islamorada house

5 12 28 nights min

  • 5 bedrooms
  • sleeps 12
  • 28 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$1,135

Price per night from

$1,135

(6) Very Good 

14

THE PERFECT GETAWAY

Florida Keys / Islamorada

Islamorada house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“The owner was understanding and worked with us” I was scheduled to rent from Dec 29th to Jan 4th and expected 7 friends to join me. For multiple personal reasons four of the seven had to back out and it is not the place you want to be without the full
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Price per night from

$357

Price per night from

$357

(9) Excellent 

30

Luxurious 3bd/3bth Villa - Your Keys Escape

Florida Keys / Marathon

Marathon villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“Marathon and Blue Heaven = Perfect Vacation!” We recently spent a week at Blue Heaven and cannot say enough good things about our experience. We were with two other couples and the floor plan worked out just great! The villa is practically brand new
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Price per night from

$302

Responds fast!
avg. 3 hours 46 minutes

Price per night from

$302

(6) Excellent 

23

Ocean pointe island retreat

Key Largo / Tavernier

Tavernier condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$197

Responds fast!
avg. 3 hours 49 minutes

Price per night from

$197

24

Key Colony Beach Home

Florida Keys / Key Colony Beach

Key Colony Beach house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$181

Price per night from

$181

47

New Rental Sombero Beach

Marathon / Marathon Shores

Marathon Shores house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$714

Price per night from

$714

(36) Very Good 

38

Key Largo 2/2 Tropical Daze Oceanfront Condo

Florida Keys / Key Largo

Key Largo apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Couldn't be better!!!” If you are looking to rest and relax, look no further.
…see more

Price per night from

$201

Responds fast!
avg. 54 minutes

Price per night from

$201

65

100 Palo De Oro Drive

Florida Keys / Islamorada

Islamorada house

4 8 28 nights min

  • 4 bedrooms
  • sleeps 8
  • 28 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$425

Price per night from

$425

(15) Very Good 

28

Family Retreat ocean front home with private pool

Florida Keys / Cudjoe Key

Cudjoe Key house

6 18 7 nights min

  • 6 bedrooms
  • sleeps 18
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool

Price per night from

$571

Price per night from

$571

(9) Excellent 

29

Oceanfront Condo - Pool, Beach, Tennis & Marina

Key Largo / Tavernier

Tavernier condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$182

Responds fast!
avg. 2 hours 10 minutes

Price per night from

$182

29

Best Kept Secret,Port Largo Villas In Key Largo,FL

Florida Keys / Key Largo

Key Largo villa

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool

Price per night from

$185

Price per night from

$185

26

Colorful beachside condo w/ shared pool & hot tub - see the ocean from your deck

Key Largo / Tavernier

Tavernier house

1 2 28 nights min

  • 1 bedroom
  • sleeps 2
  • 28 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$75

Price per night from

$75

(2) Excellent 

25

PALMS 309

Florida Keys / Islamorada

Islamorada house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$86

Price per night from

$86

(3) Very Good 

25

Dog-friendly, tropical escape with central location, hot tub, and shared pool

Florida Keys / Sugarloaf Key

Sugarloaf Key house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$151

Price per night from

$151

(49) Very Good 

291

Real World MTV House Key West

Florida Keys / Key West

Key West house

10 22 min stay varies

  • 10 bedrooms
  • sleeps 22
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals
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Price per night from

$955

Responds fast!
avg. 1 hour 52 minutes

Price per night from

$955

(1) Excellent 

24

President's Walk

Florida Keys / Key West

Key West house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$195

Price per night from

$195