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 holiday homes

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is HK$1,659
HK$2,087 total
includes taxes & fees
15 Aug - 16 Aug
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

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

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (93 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is HK$1,795
HK$4,170 total
includes taxes & fees
20 Jul - 21 Jul
SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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 HK$2,743
HK$5,326 total
includes taxes & fees
12 Aug - 13 Aug
Spanish Queen @Venture Out, Cudjoe Key

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 HK$3,293
HK$6,470 total
includes taxes & fees
12 Aug - 13 Aug
Starlight Serenity - Hideaway w Stunning Views

Ocean Blue #265 | Open-Water Views, Pet-Friendly 2BR Retreat in Venture Out

Ocean Blue #265 | Open-Water Views, Pet-Friendly 2BR Retreat in Venture Out
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Great place , incredible view. Highly recommend."
United States
Alessandro M.
The price is HK$3,703
HK$7,270 total
includes taxes & fees
26 Jul - 27 Jul
Ocean Blue #265 | Open-Water Views, Pet-Friendly 2BR Retreat in Venture Out

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (109 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
The price is HK$2,892
HK$5,561 total
includes taxes & fees
15 Aug - 16 Aug
SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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 HK$2,116
HK$4,669 total
includes taxes & fees
19 Jul - 20 Jul
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Canal-view 2BR/2BA home with pool, hot tub, and dock access.

Canal-view 2BR/2BA home with pool, hot tub, and dock access.
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 HK$1,646
HK$4,830 total
includes taxes & fees
26 Jul - 27 Jul
Canal-view 2BR/2BA home with pool, hot tub, and dock access.

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is HK$8,360
HK$14,933 total
includes taxes & fees
20 Jul - 21 Jul
Capmar House by Brightwild Huge Home Pool

Springtide House by Brightwild Waterfront Pool

Springtide House by Brightwild Waterfront Pool
2.0 star property
Raccoon Key
The price is HK$9,289
HK$15,978 total
includes taxes & fees
26 Jul - 27 Jul
Springtide House by Brightwild Waterfront Pool

Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is HK$10,335
HK$17,155 total
includes taxes & fees
11 Aug - 12 Aug
Mastway House by Brightwild Pool Dock

New Altair House by Brightwild Pool Pets

New Altair House by Brightwild Pool Pets
2.0 star property
Raccoon Key
The price is HK$8,526
HK$17,131 total
includes taxes & fees
20 Jul - 21 Jul
New Altair House by Brightwild Pool Pets

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 HK$1,646
HK$4,815 total
includes taxes & fees
16 Jul - 17 Jul
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

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 HK$3,703
HK$7,396 total
includes taxes & fees
22 Jul - 23 Jul
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is HK$9,289
HK$15,979 total
includes taxes & fees
16 Jul - 17 Jul
Waterlane House by Brightwild Pool Boat Dock

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 HK$3,086
HK$6,615 total
includes taxes & fees
18 Jul - 19 Jul
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Brand New Catchlight House With Private Pool

Brand New Catchlight House With Private Pool
2.5 star property
Raccoon Key
The price is HK$9,395
HK$18,109 total
includes taxes & fees
22 Jul - 23 Jul
Brand New Catchlight House With Private Pool

New Crestwood House by Brightwild Huge Pool

New Crestwood House by Brightwild Huge Pool
2.0 star property
Raccoon Key
The price is HK$8,561
HK$17,171 total
includes taxes & fees
21 Jul - 22 Jul
New Crestwood House by Brightwild Huge 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)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is HK$1,940
HK$4,016 total
includes taxes & fees
26 Jul - 27 Jul
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (3 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is HK$2,058
HK$5,395 total
includes taxes & fees
3 Aug - 4 Aug
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
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
756
Accommodation
392 Vacation Homes
Lowest Price
HK$2,087
Highest Price
HK$18,109

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