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Our top choices for Florida Keys vacation homes

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras
Old Town Key West
9.6 out of 10, Exceptional, (248 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
The price is AED 559
AED 1,292 total
includes taxes & fees
19 May - 20 May
May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (47 reviews)
"We absolutely loved it! "
United States
Emily B.
The price is AED 488
AED 1,280 total
includes taxes & fees
8 Jun - 9 Jun
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (37 reviews)
"We really enjoyed staying at this property"
United States
Deb P.
The price is AED 526
AED 1,489 total
includes taxes & fees
12 May - 13 May
Charming Home in Key Largo

2. Waterfront Retreat w/ Ocean Access, Key Largo!

2. Waterfront Retreat w/ Ocean Access, Key Largo!
Key Largo
10.0 out of 10, Exceptional, (16 reviews)
"My second time staying there and I will stay there in the near future! Love this place!"
United States
Alejandra S.
2. Waterfront Retreat w/ Ocean Access, Key Largo!

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

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.4 out of 10, Exceptional, (95 reviews)
"Clean and cute tiny house. Simple and easy check in at campground, very nice staff there . "
United States
Tami B.
The price is AED 575
AED 1,495 total
includes taxes & fees
19 May - 20 May
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (14 reviews)
"Location, friendly neighbors, calming courtyard."
United States
Jim C.
The price is AED 752
AED 1,963 total
includes taxes & fees
11 May - 12 May
Road's End | Prime Old Town Location! Updated Home w/ Pool

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.8 out of 10, Good, (18 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is AED 724
AED 1,652 total
includes taxes & fees
19 May - 20 May
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
8.0 out of 10, Very Good, (10 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is AED 658
AED 2,016 total
includes taxes & fees
11 May - 12 May
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is AED 1,098
AED 2,235 total
includes taxes & fees
2 Jun - 3 Jun
Paradise found

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is AED 915
AED 2,055 total
includes taxes & fees
12 May - 13 May
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Kawama G12 Upscale OceansideVilla with Marina 2/2

Kawama G12 Upscale OceansideVilla with Marina 2/2
Key Largo
10.0 out of 10, Exceptional, (9 reviews)
"We had a wonderful stay, well stocked! Our host was not easy to get a hold of, but we would definitely stay again! "
United States
Brooke B.
The price is AED 1,010
AED 2,055 total
includes taxes & fees
7 Jun - 8 Jun
Kawama G12 Upscale OceansideVilla with Marina 2/2

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (66 reviews)
"Nice location with 5 min walk to ocean view. "
United States
Trevor P.
The price is AED 768
AED 2,110 total
includes taxes & fees
10 May - 11 May
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Oceanfront Tiny Villa in the Heart of the FL Keys

Oceanfront Tiny Villa in the Heart of the FL Keys
Marathon
10.0 out of 10, Exceptional, (16 reviews)
"Very comfortable house and had everything we needed for our short stay. Would recommend! "
United States
Cheryl N.
The price is AED 768
AED 1,878 total
includes taxes & fees
10 May - 11 May
Oceanfront Tiny Villa in the Heart of the FL Keys

Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (25 reviews)
"Left to go to key west decided to stay here on our drive back up because we enjoyed it so much!"
United States
Regan C.
Charming 3-bedroom house featuring a heated private pool.

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is AED 733
AED 2,202 total
includes taxes & fees
10 May - 11 May
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is AED 951
AED 2,486 total
includes taxes & fees
31 May - 1 Jun
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (53 reviews)
"super nice and modern house, really lovely host, the kitchen is equipped with all you need for cookingall decoration is so nice fits to the beach feelingall rooms are modern and nice decoratedwe could just recommend ! if we will come back to Florida this will be again our choice!"
United States
Anonymous traveler
The price is AED 1,157
AED 2,370 total
includes taxes & fees
19 May - 20 May
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
10.0 out of 10, Exceptional, (22 reviews)
"Loved the quiet, well equipped, easy ride to all the activity in Key West. Enjoyed the French bakery and Italian restaurants within walking distance. Would most definitely return to this private townhouse....Thank you!"
United States
David M.
The price is AED 1,157
AED 3,609 total
includes taxes & fees
12 May - 13 May
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (13 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AED 771
AED 2,256 total
includes taxes & fees
9 May - 10 May
Island Time #110 Ocean Views - Cudjoe Key

SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (107 reviews)
"Had everything we needed. "
United States
Moriah W.
The price is AED 878
AED 2,006 total
includes taxes & fees
19 May - 20 May
SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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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Top Florida Keys Hotel Reviews