Cow Key Vacation Rentals

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Our top choices for Cow Key vacation homes

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
8.0 out of 10, Very good, (15 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is CA $340
CA $709 total
includes taxes & fees
Mar 23 - Mar 24
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

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, (163 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 CA $432
CA $897 total
includes taxes & fees
Mar 25 - Mar 26
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.2 out of 10, Wonderful, (9 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is CA $274
CA $826 total
includes taxes & fees
Mar 29 - Mar 30
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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

SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (106 reviews)
"Janet and Jerry were excellent hosts and the property was perfect for our trip "
United States
Shayne H.
The price is CA $314
CA $738 total
includes taxes & fees
Mar 30 - Mar 31
SAVE BIG $$$ MARCH! WATERFRONT 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, (12 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is CA $324
CA $889 total
includes taxes & fees
Apr 15 - Apr 16
Island Time #110 Ocean Views - Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (20 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 CA $480
CA $939 total
includes taxes & fees
Apr 13 - Apr 14
Spanish Queen @Venture Out, 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, (3 reviews)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
The price is CA $348
CA $668 total
includes taxes & fees
Mar 31 - Apr 1
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, 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 CA $346
CA $909 total
includes taxes & fees
Apr 20 - Apr 21
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful "
United States
Lisa P.
The price is CA $612
CA $1,255 total
includes taxes & fees
Apr 20 - Apr 21
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (154 reviews)
"Great place with beautiful views, house could use some TLC so the trade out is location and outdoor space with nice yard and very peaceful. "
United States
Peggy H.
The price is CA $480
CA $958 total
includes taxes & fees
Apr 5 - Apr 6
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

SAVE BIG $$$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (86 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is CA $534
CA $1,016 total
includes taxes & fees
Apr 3 - Apr 4
SAVE BIG $$$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (12 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 CA $343
CA $1,023 total
includes taxes & fees
Apr 18 - Apr 19
House of the Rising Sun - VO479

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 CA $1,502
CA $2,580 total
includes taxes & fees
Mar 24 - Mar 25
Private and Exclusive Florida Keys Getaway

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (33 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is CA $548
CA $1,016 total
includes taxes & fees
Apr 13 - Apr 14
Paradise found

Reel Island Retreat #273 at Venture Out in the Florida Keys

Reel Island Retreat #273 at Venture Out in the Florida Keys
Cudjoe Key
9.4 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
The price is CA $432
CA $1,026 total
includes taxes & fees
Mar 23 - Mar 24
Reel Island Retreat #273 at Venture Out in the Florida Keys

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
The price is CA $454
CA $1,055 total
includes taxes & fees
Apr 14 - Apr 15
Starlight Serenity - Hideaway with Stunning Views

105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool
Cudjoe Key
The price is CA $538
CA $1,190 total
includes taxes & fees
Mar 24 - Mar 25
105 - Newly renovated house Oceanside and Pool

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (22 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is CA $1,096
CA $2,346 total
includes taxes & fees
Mar 31 - Apr 1
The Seagate Estate at Lunara Bay

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is CA $1,096
CA $2,346 total
includes taxes & fees
Apr 14 - Apr 15
Capmar House at Lunara Bay

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
United States
Brian K.
The price is CA $1,502
CA $2,590 total
includes taxes & fees
Mar 27 - Mar 28
The Hemingway - Beach Houses Key West
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

Find out more about Cow Key

Cow Key Vacation Homes information

Number of reviews
637
Accommodation
1323 Vacation Homes
Lowest Price
CA $668
Highest Price
CA $2,590

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