Vacation Rentals & House Rentals in Florida Keys

Updating...

age 0-16
374 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

374 house rentals

3BR Oasis in the Keys w/ Kayaks & Paddle Boards - Sweeping Ocean Views!

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$303

Oceanfront condo w/beach access, shared tennis, pool, etc. - marina available!

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 40 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$82

75731 Overseas Highway

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. Brandi at Freewheeler Realestate was wonderful. She was prompt with answers to questions, friendly and professional. The home-owner obviously wants to see to it that the people staying in their home are well taken care of. Everything was great all the way down to the fluffy beach towels. We will definitely look at staying at this home again.

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$1,231

New 3 bedroom luxury condos just 10 mins from 10 beaches!!

Dry Tortugas National Park apartment

3 bedrooms / 3 bathrooms / sleeps 5

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$115

Bayside 3BR/3BA w/ Heated Pool, Dock Access, Rooftop Terrace & Stunning View

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$142

Bay Harbour D-114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$329

Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$236

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$431

Brand New 3 Story Key Largo Home

Key Largo house

5 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 1 hour 24 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$408

KEY LARGO YACHT CLUB 8

Key Largo apartment

3 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$140

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$147

Hidden Treasure

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$127

Comfortable condo w/ shared pool, private balcony, and beach access

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

“Relaxing and Fun” Very good location..steps away from Smathers beach. Parked car then rode bikes, scooters, and walked around the entire Key. Condo was very nice and comfortable with everything needed for a week or more stay. The only negative is that the in laid wood bedroom floors creek on every step--annoying at night. Maybe a few rugs could solve this issue. We really enjoyed the hot tub--relaxing.

Responds fast! avg. 40 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$305

Oceanfront Oasis with Quintessential Island Living

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 11

“Relax in Luxury” Great Location. Lots of nearby restaurants. Owners were extremely helpful in recommending attractions. A stunningly beautiful home with plenty of room for my large family to spread out. Pool was great. Swimming in warm shallow waters off of our own private beach was perfect for the kids. Pictures don't do it justice. Plenty of amenities - snorkeling gear, paddle boards, kayaks, pool toys, karaoke machine, portable waterproof sound system, etc. I have been to Florida many times always renting houses. This was by far the best.

Responds fast! avg. 3 hours 40 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$1,723

Bayview Harbor

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$185

Breezy half-duplex w/35 ft dock. Includes Cabana Club access w/ pool & beach

Key Colony Beach house

4 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 40 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$163

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$86

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 40 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$1,395

President's Walk

Key West house

2 bedrooms / 1 bathroom / sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$195

Waterfront in Key Largo, Terrific 1/1 Apt, 2nd Floor, Pet Friendly, Sleeps 4

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$75

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$113

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

Stock Island house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 40 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$217

ROCK HARBOR CLUB P-8

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$100

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

3 bedrooms / 2 bathrooms / sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$374

TWICE THE CHARM

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$183

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$262

William's Loft

Key West cottage

2 bedrooms / 1 bathroom / sleeps 3

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$87

Southard Getaway

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$195

NEW LISTING! Waterfront condo w/ shared pool and hot tub & amazing water views

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 37 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$215

Newton's Nest

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$106

Waterfront luxury Villa (42) with sunset views and boat slip

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 34 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$458

BROCK HAUS ON THE GULF

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Absolutely Beautiful and convenient for boaters!” Our family stayed here for a week in late March. We had plenty of room and everything we needed was available. This is a gorgeous condo overlooking the Florida Bay. You get to see an awesome sunset every day. We also brought our boat and the dock is literally right across the condo and ocean access is not too far away by water. Manatees visited the dock about every day, you can see picture below. We looked at other condo options and by far this was the best that suited our needs. The service provided was excellent. They were a phone call away if we needed anything. We will definitely be staying here again. Thank you so much!

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$225

Tropical 3-level, End-unit Condo With 3 Bedrooms, 3 Bathrooms Water View#

Key Largo townhouse

3 bedrooms / 3 bathrooms / sleeps 10

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$287

Dog-friendly waterfront home w/37.5-ft dock - shared pool & 2 private beaches!

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 40 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$89

Kawama P-2

Tavernier condo

3 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$247

Moon Bay A-204

Tavernier house

2 bedrooms / 1 bathroom / sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$135

Waterfront duplex w/ shared pool & beach access, 35-ft dock!

Key Colony Beach house

7 bedrooms / 8 bathrooms / sleeps 17

Responds fast! avg. 40 minutes

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$263

Artist Garden

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful House, sometimes loud” We stayed at the artist's Garden for one week. There were 4 adults and an 11 month old. The house is gorgeous, lots of interesting art. Some of it we had to move out of reach of our 11 month old, but that was easy enough. The only downside to this house is that it's located across the street from the post office. It wouldn't be bad except the bedroom windows face the post office. Some mornings the postal trucks banged around starting at 4:52 am! I finally had to put on a white noise app every night to drown them and the roosters out. (The roosters is a Key West issue, not this houses's ;-) ) .. It was in a great location, easy to access all the restaurants, Duval Street and Mallory square. The pool is very close and well maintained. We definitely would consider staying here again, but if a different house in Truman annex were available not close to the post office, we'd probably choose that first. We would definitely go through at Home in Key West, though! They were wonderful and helpful. They also recommended using The Hip Tourist for renting baby equipment and it was perfect!!!

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$285

Viewing 38 of 374
rentals in Florida Keys

×

Also consider