Cow Key Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Cow Key vacation homes
1. Poolside Cottage #412
Poolside Cottage #412Key West
9.4 out of 10, Exceptional, (38 reviews)
"Wonderful stay. Thank you."
shannon b.
The price is CA $261
CA $446 total
includes taxes & fees
Dec 1 - Dec 2
2. Poolside Cottage #411
Poolside Cottage #411Key West
9.8 out of 10, Exceptional, (72 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
Jennifer W.
The price is CA $261
CA $446 total
includes taxes & fees
Dec 1 - Dec 2
3. Casa Havana | Old Town Condo w/ Pool & Balcony
Casa Havana | Old Town Condo w/ Pool & BalconyOld Town Key West
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
Kim T.
The price is CA $273
CA $1,022 total
includes taxes & fees
Nov 16 - Nov 17
4. Road's End | Prime Old Town Location! Updated Home w/ Pool
Road's End | Prime Old Town Location! Updated Home w/ PoolOld Town Key West
9.6 out of 10, Exceptional, (28 reviews)
"Charming, clean accommodations in a conveniently located area of Key West for walking to sites and renting bicycles"
BARBARA Y.
The price is CA $210
CA $596 total
includes taxes & fees
Nov 15 - Nov 16
5. Sea Esta Suite | Located On Iconic Duval w/ Pool
Sea Esta Suite | Located On Iconic Duval w/ PoolOld Town Key West
9.8 out of 10, Exceptional, (58 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
Rick H.
The price is CA $273
CA $1,022 total
includes taxes & fees
Nov 10 - Nov 11
6. Slice of Paradise
Slice of ParadiseStock Island
10.0 out of 10, Exceptional, (5 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
Cathy S.
The price is CA $367
CA $788 total
includes taxes & fees
Nov 10 - Nov 11
7. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRSStock Island
9.6 out of 10, Exceptional, (139 reviews)
"We had an awesome stay! We enjoyed being able to use the bikes and have covered parking, too. We would definitely stay here again!"
Melanie K.
The price is CA $312
CA $718 total
includes taxes & fees
Nov 9 - Nov 10
8. Gone Coastal
Gone CoastalStock Island
9.6 out of 10, Exceptional, (22 reviews)
"Great place , clean and close to everything!"
april
The price is CA $380
CA $802 total
includes taxes & fees
Dec 7 - Dec 8
9. Waterlane House at Lunara Bay
Waterlane House at Lunara BayRaccoon Key
9.8 out of 10, Exceptional, (38 reviews)
"Everything was great"
Justin S.
The price is CA $1,129
CA $2,359 total
includes taxes & fees
Nov 18 - Nov 19
10. Capmar House at Lunara Bay
Capmar House at Lunara BayRaccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The Best VRBO I have stayed in "
Wilbert C.
The price is CA $846
CA $2,008 total
includes taxes & fees
Nov 10 - Nov 11
11. The Seagate Estate at Lunara Bay
The Seagate Estate at Lunara BayRaccoon Key
10.0 out of 10, Exceptional, (30 reviews)
"Great property, terrific hosts - amazing location!"
Jason T.
The price is CA $1,129
CA $2,359 total
includes taxes & fees
Nov 16 - Nov 17
12. Spacious 3-bedroom townhome on Stock Island with resort style pool.
Spacious 3-bedroom townhome on Stock Island with resort style pool.Stock Island
10.0 out of 10, Exceptional, (8 reviews)
"Perfect for our family trip to Key West. Great location and we enjoyed the pool and nearby restaurants. Easy check in and check out process and clear, timely communication with the owner. "
Samantha P.
The price is CA $422
CA $888 total
includes taxes & fees
Dec 9 - Dec 10
13. Evershore House Pool Parking Dock
Evershore House Pool Parking DockRaccoon Key
The price is CA $1,085
CA $2,200 total
includes taxes & fees
Nov 24 - Nov 25
14. Aquaria House at Lunara Bay
Aquaria House at Lunara BayRaccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"Beautiful, amazing property which we enjoyed so much and we cannot wait to return!Perfect location!"
Elizabeth E.
The price is CA $846
CA $1,960 total
includes taxes & fees
Nov 9 - Nov 10
15. Mastway House at Lunara Bay - Wellness Home
Mastway House at Lunara Bay - Wellness HomeRaccoon Key
9.6 out of 10, Exceptional, (36 reviews)
"My family and I had a very nice stay."
Robert L.
The price is CA $846
CA $2,008 total
includes taxes & fees
Nov 10 - Nov 11
16. Spindrift House at Lunara Bay
Spindrift House at Lunara BayRaccoon Key
10.0 out of 10, Exceptional, (35 reviews)
"Property was good would stay here again!"
Richard K.
The price is CA $846
CA $1,960 total
includes taxes & fees
Nov 9 - Nov 10
17. The Shellstone House at Solaire Lunara Bay
The Shellstone House at Solaire Lunara BayRaccoon Key
10.0 out of 10, Exceptional, (7 reviews)
"Great property / location. Perfect house with wonderful amenities!!!"
Dudley S.
The price is CA $1,411
CA $3,145 total
includes taxes & fees
Nov 10 - Nov 11
18. Suncoast House at Lunara Bay
Suncoast House at Lunara BayRaccoon Key
9.6 out of 10, Exceptional, (44 reviews)
"Beautiful House, super clean, perfect location "
carlos s.
The price is CA $846
CA $2,191 total
includes taxes & fees
Nov 9 - Nov 10
19. Evershore Estate at Lunara Bay | Wellness Home
Evershore Estate at Lunara Bay | Wellness HomeRaccoon Key
9.8 out of 10, Exceptional, (30 reviews)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
John F.
The price is CA $846
CA $2,008 total
includes taxes & fees
Nov 24 - Nov 25
20. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated AccessCudjoe 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."
Cheryl V.
The price is CA $200
CA $594 total
includes taxes & fees
Nov 13 - Nov 14
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.
Find vacation rentals that suit your style
Aparthotels
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Cow Key Hotel Reviews
Casa Marina Key West, Curio Collection by Hilton
10/10 Excellent
Find out more about Cow Key
Cow Key Vacation Homes information
Number of reviews | 620 |
|---|---|
Accommodation | 1204 Vacation Homes |
Lowest Price | CA $446 |
Highest Price | CA $3,145 |
Explore a world of travel with Expedia
- Motels in Key West
- Hotels near Duval Street
- Beach Hotel Hotels in Key West
- Aparthotels in Marathon
- Vacation Homes in Key West
- Motel 6 Hotels in Key West
- Vacation Homes in Monroe County
- Adults Only Resorts & in Key West
- Villas in Summerland Key
- Houseboats in Key West
- Villas in Key West
- Houseboats in Marathon
- Family Hotels in Key West
- Cheap Hotels in Key West
- Oceanfront Hotels in Key West
- Resorts in Big Pine Key
- Apartments in Sugarloaf Key
- Key West Hotels
- Villas in Key Haven
- Condo Rentals in Marathon
- Lgbt Friendly Hotels in Key West
- Guest Houses in Key West
- Cruise Ships in Key West
- Condo Rentals in Key West
- Cottages in Key West
- Cottages in Marathon
- Hotels near Key West Intl.
- Lodges in Key Colony Beach
- All Inclusive Resorts and in Key West
- Pet-Friendly Hotels in Key West
- B&B in Key West
- Apartments in Key West
- Resorts in Key West
- Houseboats in Cow Key
- Cabin Rentals in Marathon
- Resorts in Cudjoe Key
- Condo Resorts in Key West
- Motels in Key Haven
- Cabin Rentals in Key West
- Motels in Marathon
- Cabin Rentals in No Name Key
- Cabin Rentals in Boca Chica Key
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Halifax (YHZ) to Key West (EYW)
- Flights from Syracuse (SYR) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- Flights from Bangor (BGR) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from Niagara Falls (IAG) to Key West (EYW)
- Flights from Cancun (CUN) to Key West (EYW)
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Saskatoon (YXE) to Key West (EYW)
- Flights from Cincinnati (CVG) to Key West (EYW)
- Flights from Toronto (YYZ) to Key West (EYW)
- Flights from Ottawa (YOW) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from San Francisco (SFO) to Key West (EYW)
- Flights from Hamilton (YHM) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from Naples (APF) to Key West (EYW)
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Kailua-Kona (KOA) to Key West (EYW)
- Flights from London (YXU) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Edmonton (YEG) to Key West (EYW)
- Flights from Vancouver (YVR) to Key West (EYW)
- Flights from Windsor (YQG) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from Toronto (YTZ) to Key West (EYW)
- Flights from St. Petersburg (PIE) to Key West (EYW)
- Flights to Key West
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Seattle (SEA) to Key West (EYW)
- Flights from Daytona Beach (DAB) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from Richmond (RIC) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Montreal (YUL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Calgary (YYC) to Key West (EYW)
- Flights from Regina (YQR) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)