A coastal road with a beach on one side and a marina with boats on the other.

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Our top choices for Summerland Key vacation homes

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
The price is ¥3,727
¥60,180 total
includes taxes & fees
Jul 18 - Jul 19
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (148 reviews)
"Nice property in a beautiful location. Great place to sit and enjoy the scenery and activities. "
United States
Andy D.
The price is ¥76,233
¥152,882 total
includes taxes & fees
Jul 6 - Jul 7
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is ¥30,478
¥95,246 total
includes taxes & fees
Jul 6 - Jul 7
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

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, (173 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 ¥50,822
¥105,416 total
includes taxes & fees
Jul 5 - Jul 6
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

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, (30 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is ¥38,117
¥104,515 total
includes taxes & fees
Aug 3 - Aug 4
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is ¥50,443
¥113,651 total
includes taxes & fees
Jul 7 - Jul 8
Starlight Serenity - Hideaway w Stunning Views

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)
"Everything was perfect location house amenities Really enjoyed our time there"
United States
Matt S.
The price is ¥33,833
¥75,172 total
includes taxes & fees
Jul 6 - Jul 7
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (56 reviews)
"We loved our stay! Prime location"
United States
Lacey C.
The price is ¥61,834
¥144,950 total
includes taxes & fees
Jul 6 - Jul 7
Post Card Point #319 - Ocean Views!

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 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 ¥56,469
¥109,792 total
includes taxes & fees
Jul 6 - Jul 7
Spanish Queen @Venture Out, Cudjoe Key

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
Cudjoe Key
9.6 out of 10, Exceptional, (53 reviews)
"Our stay was wonderful. Accommodations were as described and very comfortable. Location was great and the best views for the sunrise. "
United States
Kathy A.
The price is ¥59,292
¥131,564 total
includes taxes & fees
Jul 6 - Jul 7
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

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

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (91 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is ¥40,174
¥90,270 total
includes taxes & fees
Aug 1 - Aug 2
SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.4 out of 10, Exceptional, (3 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is ¥33,865
¥100,185 total
includes taxes & fees
Jul 12 - Jul 13
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool
Cudjoe Key
The price is ¥63,859
¥139,845 total
includes taxes & fees
Aug 2 - Aug 3
105 - Newly renovated house Oceanside and Pool

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (101 reviews)
"Wonderful location and as described. Hope to be back soon."
United States
Anne H.
The price is ¥54,425
¥120,129 total
includes taxes & fees
Jul 22 - Jul 23
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Cudjoe Key
8.0 out of 10, Very Good, (2 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is ¥33,881
¥100,234 total
includes taxes & fees
Jul 6 - Jul 7
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

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, (161 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is ¥43,562
¥95,634 total
includes taxes & fees
Jul 15 - Jul 16
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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 ¥56,469
¥139,841 total
includes taxes & fees
Jul 6 - Jul 7
House of the Rising Sun - VO479

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 ¥27,092
¥91,114 total
includes taxes & fees
Jul 8 - Jul 9
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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 ¥29,646
¥94,340 total
includes taxes & fees
Jul 15 - Jul 16
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Great place! Perfect location"
United States
Troy B.
The price is ¥50,822
¥120,422 total
includes taxes & fees
Aug 3 - Aug 4
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
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 Summerland Key Hotel Reviews

Find out more about Summerland Key

Summerland Key Vacation Homes information

Number of reviews
141
Accommodation
392 Vacation Homes
Lowest Price
¥46,082
Highest Price
¥596,867