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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Cow Key vacation homes

House | 8 bedrooms, Internet

Vacation Home in Raccoon Key

The Fairhaven House at Solaire Lunara Bay
2.0 star property
The Fairhaven House at Solaire Lunara Bay
Interior

Vacation Home in Raccoon Key

The Shellstone House at Solaire Lunara Bay
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home with great outdoor space and we loved the pool and private dock"
United States
Sharon L.
The price is AED 5,858
AED 10,969 total
includes taxes & fees
19 Jan - 20 Jan
The Shellstone House at Solaire Lunara Bay
A heated pool

Vacation Home in Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
2.5 star property
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is AED 733
AED 2,220 total
includes taxes & fees
19 Jan - 20 Jan
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Exterior

Vacation Home in Cudjoe Key

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
9.4 out of 10, Exceptional, (101 reviews)
"Great location. "
United States
Davian k.
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool

Vacation Home in Sugarloaf Key

Azucar - Beach Houses Key West
10.0 out of 10, Exceptional, (10 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
Azucar - Beach Houses Key West
Beach towels

Vacation Home in Cudjoe Key

Relax by Florida Keys Beaches, just a 7-min drive away
9.8 out of 10, Exceptional, (198 reviews)
"Will definitely stay here again "
United States
Jeannine R.
The price is AED 744
AED 2,072 total
includes taxes & fees
18 Jan - 19 Jan
Relax by Florida Keys Beaches, just a 7-min drive away
Exterior

Vacation Home in Cudjoe Key

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
8.8 out of 10, Excellent, (157 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
The price is AED 992
AED 2,174 total
includes taxes & fees
19 Jan - 20 Jan
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
A heated pool

Vacation Home in Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is AED 1,253
AED 2,857 total
includes taxes & fees
18 Jan - 19 Jan
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Fridge, microwave, oven, stovetop

Vacation Home in Raccoon Key

Larkshine House at Lunara Bay
2.0 star property
10.0 out of 10, Exceptional, (8 reviews)
"well maintained, clean, easy to access"
United States
Raj P.
The price is AED 5,491
AED 10,349 total
includes taxes & fees
21 Jan - 22 Jan
Larkshine House at Lunara Bay
Outdoor dining

Vacation Home in Cudjoe Key

135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Our house was beautiful and right on the water! Great sunrises and beautiful views! Fully equipped with everything you need or want! This home is the best VRBO we have rented! Would love to come back!!"
United States
Loretta F.
The price is AED 845
AED 2,511 total
includes taxes & fees
28 Jan - 29 Jan
135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
House | 2 bedrooms, Internet

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
The price is AED 1,312
AED 2,771 total
includes taxes & fees
21 Jan - 22 Jan
Starlight Serenity - Hideaway w Stunning Views
A heated pool

Vacation Home in Cudjoe Key

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
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 1,253
AED 2,850 total
includes taxes & fees
24 Jan - 25 Jan
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Pool

Vacation Home in Raccoon Key

The Seagate Estate at Lunara Bay
10.0 out of 10, Exceptional, (19 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is AED 2,567
AED 5,815 total
includes taxes & fees
19 Jan - 20 Jan
The Seagate Estate at Lunara Bay
Property grounds

Vacation Home in Cudjoe Key

Cudjoe Cottages, swimming pool, just 20 miles from Key West
8.8 out of 10, Excellent, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is AED 1,194
AED 2,445 total
includes taxes & fees
20 Jan - 21 Jan
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Exterior

Vacation Home in Cudjoe Key

Southern Exposure in Cudjoe Key #49
2.0 star property
7.6 out of 10, Good, (4 reviews)
"The house is nice and sitting on the balcony feels like you're floating. It was a nice place to stay"
United States
Colleen G.
The price is AED 887
AED 2,500 total
includes taxes & fees
8 Feb - 9 Feb
Southern Exposure in Cudjoe Key #49
Outdoor pool, a heated pool

Vacation Home in Cudjoe Key

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
7.6 out of 10, Good, (13 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is AED 1,010
AED 1,977 total
includes taxes & fees
4 Feb - 5 Feb
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Exterior

Vacation Home in Cudjoe Key

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is AED 1,098
AED 2,232 total
includes taxes & fees
18 Jan - 19 Jan
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Exterior

Vacation Home in Cudjoe Key

105 - Newly renovated house Oceanside and Pool
105 - Newly renovated house Oceanside and Pool
Outdoor pool, a heated pool

Vacation Home in Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is AED 1,286
AED 2,485 total
includes taxes & fees
16 Feb - 17 Feb
Spanish Queen @Venture Out, Cudjoe Key
TV, stereo, offices

Vacation Home in Raccoon Key

Floralee House at Lunara Bay
2.0 star property
9.8 out of 10, Exceptional, (8 reviews)
"Amazing house! Spacious, great pool, & good location "
United States
Paige G.
The price is AED 3,302
AED 7,677 total
includes taxes & fees
19 Jan - 20 Jan
Floralee House at Lunara Bay
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

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"New hotel with all amenities. Need a car to get around or use shuttle to get to a drop off point in Historic Key West District, a place for everyone. Friendly people."
Dedra 4-night trip
Posted 2 days ago
The Perry Hotel & Marina Key West