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Our top choices for Summerland Key holiday homes

9.4 out of 10, Exceptional, (104 reviews)
"Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. "
United States
Lauren D.
The price is HK$2,338
HK$4,839 total
includes taxes & fees
30 Mar - 31 Mar
SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
9.2 out of 10, Wonderful, (9 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is HK$1,560
HK$4,758 total
includes taxes & fees
29 Mar - 30 Mar
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
9.8 out of 10, Exceptional, (123 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is HK$1,681
HK$4,117 total
includes taxes & fees
5 Apr - 6 Apr
Kelly's Kabin - Adorable Private Summerland Key Cottage
8.8 out of 10, Excellent, (162 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
The price is HK$2,737
HK$5,456 total
includes taxes & fees
26 Mar - 27 Mar
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Holiday Home in Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
9.4 out of 10, Exceptional, (19 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 HK$2,737
HK$5,353 total
includes taxes & fees
23 Mar - 24 Mar
Spanish Queen @Venture Out, Cudjoe Key

Holiday Home in Cudjoe Key

Fun in the Sun in Cudjoe Key! #51
8.6 out of 10, Excellent, (9 reviews)
"This was a beautiful"
United States
Debbie A.
The price is HK$1,799
HK$5,339 total
includes taxes & fees
15 Mar - 16 Mar
Fun in the Sun in Cudjoe Key! #51
The price is HK$2,053
HK$5,320 total
includes taxes & fees
1 Apr - 2 Apr
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
7.8 out of 10, Good, (14 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is HK$1,935
HK$4,031 total
includes taxes & fees
20 Mar - 21 Mar
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
8.8 out of 10, Excellent, (153 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is HK$2,933
HK$5,700 total
includes taxes & fees
5 Apr - 6 Apr
Cudjoe Cottages, swimming pool, just 20 miles from Key West
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 HK$2,072
HK$3,921 total
includes taxes & fees
1 Apr - 2 Apr
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
8.0 out of 10, Very good, (1 review)
" 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.
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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 HK$1,848
HK$5,058 total
includes taxes & fees
1 Apr - 2 Apr
Island Time #110 Ocean Views - Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is HK$2,258
HK$5,637 total
includes taxes & fees
6 Apr - 7 Apr
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on 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 HK$2,053
HK$5,320 total
includes taxes & fees
2 Apr - 3 Apr
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful "
United States
Lisa P.
The price is HK$4,311
HK$8,150 total
includes taxes & fees
30 Mar - 31 Mar
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Holiday Home in Upper Sugarloaf Key

Private and Exclusive Florida Keys Getaway
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is HK$8,559
HK$14,700 total
includes taxes & fees
24 Mar - 25 Mar
Private and Exclusive Florida Keys Getaway
The price is HK$2,737
HK$6,124 total
includes taxes & fees
12 Mar - 13 Mar
Starlight Serenity - Hideaway with Stunning Views
9.6 out of 10, Exceptional, (97 reviews)
"Loved the location, good communication!"
United States
Cindy P.
The price is HK$3,519
HK$6,940 total
includes taxes & fees
29 Mar - 30 Mar
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, (85 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is HK$3,042
HK$5,724 total
includes taxes & fees
3 Apr - 4 Apr
SAVE BIG $$$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Holiday Home in Upper Sugarloaf Key

The Hemingway - Beach Houses Key West
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 HK$11,140
HK$18,530 total
includes taxes & fees
12 Mar - 13 Mar
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 Summerland Key Hotel Reviews

Find out more about Summerland Key

Summerland Key Vacation Homes information

Number of reviews
599
Accommodation
411 Vacation Homes
Lowest Price
HK$3,921
Highest Price
HK$18,530

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