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Our top choices for Cow Key vacation homes

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is AED 656
AED 2,111 total
includes taxes & fees
9 May - 10 May
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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

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

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

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very Good, (3 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is AED 771
AED 2,282 total
includes taxes & fees
9 May - 10 May
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near 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.
Paradise found

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
20 May - 21 May
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (25 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is AED 1,286
AED 2,514 total
includes taxes & fees
8 Jun - 9 Jun
Spanish Queen @Venture Out, Cudjoe Key

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 2,217 total
includes taxes & fees
20 May - 21 May
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is AED 926
AED 2,459 total
includes taxes & fees
19 May - 20 May
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

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

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (107 reviews)
"Had everything we needed. "
United States
Moriah W.
The price is AED 878
AED 2,006 total
includes taxes & fees
20 May - 21 May
SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Cudjoe Key
9.2 out of 10, Wonderful, (9 reviews)
"Great place! Perfect location"
United States
Troy B.
The price is AED 868
AED 2,376 total
includes taxes & fees
9 May - 10 May
Salty Breeze #161 - Canal Front Venture Out Home on 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 973
AED 2,514 total
includes taxes & fees
2 Jun - 3 Jun
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is AED 2,121
AED 4,360 total
includes taxes & fees
10 May - 11 May
Private and Exclusive Florida Keys Getaway

Mirador House at Lunara Bay

Mirador House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (35 reviews)
"Great trip! The kids loved the pool and we really enjoyed biking around Key West. Fun to have our boat there too! Thanks for the great memories! "
United States
Andrea M.
The price is AED 1,833
AED 5,513 total
includes taxes & fees
11 May - 12 May
Mirador House at Lunara Bay

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (23 reviews)
"Great place and great hosts. However the pool never heated and couldn’t get anyone out to look at it. Overall an amazing stay and would definitely return."
United States
Austin S.
The price is AED 2,935
AED 6,279 total
includes taxes & fees
7 Jun - 8 Jun
The Seagate Estate at Lunara Bay

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (167 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is AED 1,286
AED 2,563 total
includes taxes & fees
3 Jun - 4 Jun
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"It was great. House was amazing"
United States
Ernest H.
The price is AED 2,935
AED 6,272 total
includes taxes & fees
7 Jun - 8 Jun
Springtide House at Lunara Bay

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is AED 2,808
AED 5,432 total
includes taxes & fees
18 May - 19 May
The Lighthouse - Beach Houses Key West

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is AED 2,554
AED 5,555 total
includes taxes & fees
19 May - 20 May
Capmar House by Brightwild Huge Home Pool

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (14 reviews)
"We rented a boat, fished and snorkeled. Really enjoyed the patio right on the sea wall. One of the best parts of property was the stunning view of the morning sunrise!"
United States
Matt W.
The price is AED 1,286
AED 3,165 total
includes taxes & fees
9 May - 10 May
House of the Rising Sun - VO479
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 Cow Key Hotel Reviews

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