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Top Holiday Rentals in Florida Keys

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (57)
"We stayed here in April 2025 - perfect location with a great patio overlooking the waterfront harbor, perfect for us. Everything you need is a short drive - grocery Publix is close enough to walk to. The tiny house is adorable and clean, well stocked kitchen - We found great place to hike /Hamock State Park and Rowell’s was a great place to swim "
The price is £299
includes taxes & fees
7 Jul - 8 Jul
Waterfront Tiny House w Pool, Beach, and Boat Dock

Experience Island Living in a Relaxed Room Setting! Outdoor and Parking Onsite!

The price is £168
includes taxes & fees
7 Jul - 8 Jul
Experience Island Living in a Relaxed Room Setting! Outdoor and Parking Onsite!

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (117)
"This was our second time staying here. Feels very secluded although it's right off the highway. We saw many Key deer on our way to No Name Pub , including babies who thougt we should feed them) (We did not feed them). Highly recommend!"
The price is £370
includes taxes & fees
11 Jul - 12 Jul
Kelly's Kabin - Adorable Private Summerland Key Cottage

Kingfish Keep | Lively Escape on Duval! Balcony!

10.0 out of 10, Exceptional, (14)
"It was everything it needed to be. Great place. Great location"
The price is £245
includes taxes & fees
6 Jul - 7 Jul
Kingfish Keep | Lively Escape on Duval! Balcony!

Poolside Cottage #411

9.8 out of 10, Exceptional, (47)
"Lovely home to stay in for a couple of nights on Key West"
The price is £254
includes taxes & fees
8 Jul - 9 Jul
Poolside Cottage #411

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (4)
"The Blue Lobster is a gem. Clean, cute, enough room to spread out and every extra provided to make your stay comfortable. Community is friendly and has a nice pool, hot tubs and pickle ball courts. Loved it here. "
The price is £465
includes taxes & fees
8 Jul - 9 Jul
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Paradise found

9.8 out of 10, Exceptional, (25)
"Clean, quiet and great location near Key West. "
The price is £363
includes taxes & fees
31 Jul - 1 Aug
Paradise found

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (68)
"Great tiny house, enjoyed our stay"
The price is £301
includes taxes & fees
4 Aug - 5 Aug
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Villa 5053 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (44)
"We had a good stay. Nice place"
The price is £432
includes taxes & fees
7 Jul - 8 Jul
Villa 5053 on Duck Key BOAT SLIP available

Charming Home in Key Largo

9.6 out of 10, Exceptional, (19)
"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "
The price is £333
includes taxes & fees
12 Jul - 13 Jul
Charming Home in Key Largo

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (80)
"Great atmosphere, right on a canal. A perfect and comfortable home!"
The price is £372
includes taxes & fees
6 Jul - 7 Jul
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Feb 3-10 $245 off the rates close beach full kitchen & patio

9.6 out of 10, Exceptional, (220)
"The host was very friendly and easy to communicate with. Excellent property in a great neighborhood! Will definitely consider staying here again."
The price is £233
includes taxes & fees
13 Jul - 14 Jul
Feb 3-10 $245 off the rates close beach full kitchen & patio

Keys 3 Bedroom Corner Home near Beach & Key West

9.6 out of 10, Exceptional, (8)
"Great location, right in the middle keys, easy access to everything. "
The price is £470
includes taxes & fees
6 Jul - 7 Jul
Keys 3 Bedroom Corner Home near Beach & Key West

Beach House Getaway - Kayaks & 2-2.5 Villa

9.8 out of 10, Exceptional, (28)
"Great location for day trips and very clean, well stocked apartment. "
The price is £374
includes taxes & fees
13 Jul - 14 Jul
Beach House Getaway - Kayaks & 2-2.5 Villa

Villa 5103 on Duck Key BOAT SLIP available

9.4 out of 10, Exceptional, (53)
"Our stay was great. The place had ampule room, a great view, the bath area had lots of towels that were a good quality. We enjoyed going to the "
The price is £436
includes taxes & fees
3 Aug - 4 Aug
Villa 5103 on Duck Key BOAT SLIP available

Kawama L4 - Upscale Oceanside Villa with Marina

9.6 out of 10, Exceptional, (136)
"This property was perfect in the heart of key largo with pool and ocean access. Had everything we need and even included two bikes! Great stay overall!"
Kawama L4 - Upscale Oceanside Villa with Marina

Aquaria House by Brightwild Pool Boat Dock

2.0 star property
The price is £1,415
includes taxes & fees
16 Jul - 17 Jul
Aquaria House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock

2.0 star property
The price is £1,415
includes taxes & fees
15 Jul - 16 Jul
Waterlane House by Brightwild Pool Boat Dock

Tiny Villa, Big Ocean Views| Breathtaking Sunsets

10.0 out of 10, Exceptional, (13)
"Our stay at the tiny villa was wonderful. The property was as listed and had fantastic views. Communication with the property owner was very easy. We really enjoyed our time in Duck Key."
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Brand New Build Larkshine House - Pool

2.0 star property
The price is £3,230
includes taxes & fees
20 Jul - 21 Jul
Brand New Build Larkshine House - Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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