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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sep - 6 Sep

Our top choices for Stock Island vacation homes

Pool

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 2,213 total
includes taxes & fees
2 Jun - 3 Jun
Paradise found
Property grounds

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)
"Great spot , only a short drive downtown. Condo was excellent, clean and kept up beautifully. Had everything you needed and was a great place to spend the week"
United States
William H.
The price is AED 1,157
AED 3,631 total
includes taxes & fees
19 May - 20 May
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Pool

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, (5 reviews)
"Location, pool, comfy beds. Will definitely return and recommend to others "
United States
janet n.
The price is AED 1,319
AED 2,520 total
includes taxes & fees
20 May - 21 May
Spacious 3-bedroom townhome on Stock Island with resort style pool.
Pool

Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (1 review)
"As beautiful as the photos"
United States
Sheila S.
The price is AED 889
AED 1,982 total
includes taxes & fees
19 May - 20 May
Slice of Paradise
Outdoor pool

Gone Coastal

Gone Coastal
Stock Island
9.8 out of 10, Exceptional, (21 reviews)
"Great place , clean and close to everything!"
United States
april
Gone Coastal
Interior

3-bedroom townhome in Key West with fitness room, WiFi

3-bedroom townhome in Key West with fitness room, WiFi
Stock Island
9.8 out of 10, Exceptional, (13 reviews)
"Nicely furnished with everything you could need. Great location with an easy drive into downtown. Facilities kept up well and we felt very safe with the gated entrance."
United States
Sharon B.
The price is AED 1,862
AED 4,222 total
includes taxes & fees
1 Jun - 2 Jun
3-bedroom townhome in Key West with fitness room, WiFi
A heated pool

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 2,133 total
includes taxes & fees
24 May - 25 May
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Exterior

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

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (88 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is AED 915
AED 2,048 total
includes taxes & fees
19 May - 20 May
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
The price is AED 790
AED 1,945 total
includes taxes & fees
10 Jun - 11 Jun
Kelly's Kabin - Adorable Private Summerland Key Cottage
Exterior detail

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 813
AED 2,312 total
includes taxes & fees
17 May - 18 May
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Outdoor pool, a heated 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, (20 reviews)
"Online photos did not match the house. You entered the house through one of the bedrooms. So privacy for those staying in that room did not exist. The extra you pay when checking in for the club amenities was not worth the expense. "
United States
Seth
The price is AED 721
AED 1,659 total
includes taxes & fees
27 May - 28 May
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Exterior

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

SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (108 reviews)
"Had everything we needed. "
United States
Moriah W.
The price is AED 731
AED 1,819 total
includes taxes & fees
20 May - 21 May
SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor dining

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 2,282 total
includes taxes & fees
21 May - 22 May
Island Time #110 Ocean Views - Cudjoe Key
A heated 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 2,206 total
includes taxes & fees
17 May - 18 May
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Outdoor pool, a heated pool

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 2,499 total
includes taxes & fees
18 May - 19 May
Spanish Queen @Venture Out, Cudjoe Key
Marina

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, (168 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 2,555 total
includes taxes & fees
3 Jun - 4 Jun
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Pool

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 4,356 total
includes taxes & fees
27 May - 28 May
Private and Exclusive Florida Keys Getaway
A heated pool

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 2,477 total
includes taxes & fees
21 May - 22 May
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Property grounds

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, (156 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 AED 1,194
AED 2,445 total
includes taxes & fees
2 Jun - 3 Jun
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Terrace/patio

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 3,173 total
includes taxes & fees
18 May - 19 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 Stock Island Hotel Reviews

Havana Cabana at Key West

Havana Cabana at Key West

10/10 Excellent
"The breakfast was delicious. The hot tub was warrmer than I would have liked but was enjoyable. The staff was bery helpful and always friendly. I truly enjoyed relaxing and swimming in the pool the most."
Nancy 3-night trip
Posted 3 hours ago
Havana Cabana at Key West