Search Vacation Homes in Summerland Key

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Summerland Key

🌴 TROPICAL RETREAT 🌴 RV in the Keys

10.0 out of 10, Exceptional, (1)
"Its clean and plenty of room.Outdoor seating is wonderful. Could use a gas grill. But definitely a great place."
The price is AED 493
AED 1,207 total
includes taxes & fees
1 Sep - 2 Sep
🌴 TROPICAL RETREAT 🌴 RV in the Keys

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is AED 896
AED 2,184 total
includes taxes & fees
31 Aug - 1 Sep
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (98)
"This is a great place to stay, neighborhood is nice, very convenient with the marina and boat ramp on site. I would definitely stay here again. "
The price is AED 621
AED 1,695 total
includes taxes & fees
1 Sep - 2 Sep
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (152)
"The place was spacious, very clean and beautiful!"
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (81)
"The house was clean as a whistle, has tons of storage, came with everything you need, and is well located. Our husbands really loved the boat launch and docking, the pool and amenities are well kept, security in the park was well done, and the owner are very pleasant and responsive."
The price is AED 657
AED 1,744 total
includes taxes & fees
1 Sep - 2 Sep
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (237)
"Clean and inviting property, great location, attentive host. Highly recommend."
The price is AED 1,286
AED 3,003 total
includes taxes & fees
31 Aug - 1 Sep
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

10.0 out of 10, Exceptional, (2)
"Absolutely love it here… Randy is great to work with and always available. "
The price is AED 803
AED 1,624 total
includes taxes & fees
1 Sep - 2 Sep
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Sailfish Haven #390 - Ocean Views, 35' seawall

8.8 out of 10, Excellent, (6)
"Property clean, well stocked."
The price is AED 877
AED 2,159 total
includes taxes & fees
2 Sep - 3 Sep
Sailfish Haven #390 - Ocean Views, 35' seawall

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (7)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is AED 973
AED 2,282 total
includes taxes & fees
2 Sep - 3 Sep
Island Time #110 Ocean Views - Cudjoe Key

Reel Island Retreat #273 at Venture Out in the Florida Keys

9.6 out of 10, Exceptional, (7)
"The staff at Venture one was absolutely amazing. The home we stayed in was also a great location. Dated but clean. Definitely will stay at Venture again !"
The price is AED 973
AED 2,282 total
includes taxes & fees
2 Sep - 3 Sep
Reel Island Retreat #273 at Venture Out in the Florida Keys

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

2.0 star property
9.0 out of 10, Wonderful, (7)
"Loved the location! Very nice park. Our place had an amazing view to watch the sunrise and to enjoy a nice home cooked meal before heading up to the pool."
The price is AED 973
AED 2,282 total
includes taxes & fees
2 Sep - 3 Sep
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (119)
"We enjoyed our stay in Kelly's Kabin. The house was very clean and comfortable, and was in a great location for exploring the mid to lower Keys. "
The price is AED 753
AED 1,900 total
includes taxes & fees
28 Sep - 29 Sep
Kelly's Kabin - Adorable Private Summerland Key Cottage

Private and Exclusive Beach Getaway

10.0 out of 10, Exceptional, (1)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
The price is AED 3,837
AED 7,228 total
includes taxes & fees
31 Aug - 1 Sep
Private and Exclusive Beach Getaway

Galleon Getaway #533- Oceanfront Community

The price is AED 742
AED 1,988 total
includes taxes & fees
31 Aug - 1 Sep
Galleon Getaway #533- Oceanfront Community

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

9.4 out of 10, Exceptional, (26)
"Close to Key West and lots of great boating"
The price is AED 973
AED 2,282 total
includes taxes & fees
2 Sep - 3 Sep
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Mahi House #440 - 35' seawall

10.0 out of 10, Exceptional, (1)
"The house was just right. Nice community. Quiet and peaceful. Just what we needed. The host was kind and responsive. "
The price is AED 954
AED 2,256 total
includes taxes & fees
2 Sep - 3 Sep
Mahi House #440 - 35' seawall

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

9.8 out of 10, Exceptional, (8)
"Beautiful place!"
The price is AED 1,552
AED 3,013 total
includes taxes & fees
31 Aug - 1 Sep
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

The Lighthouse - Beach Houses Key West

9.6 out of 10, Exceptional, (11)
"We saved up for 3 years for this trip and this property did not disappoint! Thank you for sharing your beautiful piece of paradise with us!"
The Lighthouse - Beach Houses Key West

Spanish Queen @Venture Out, Cudjoe Key

9.4 out of 10, Exceptional, (19)
"We enjoyed our stay at venture out at the Spanish main residence it was lovely and we are going to return again next year"
The price is AED 1,286
AED 2,514 total
includes taxes & fees
1 Sep - 2 Sep
Spanish Queen @Venture Out, Cudjoe Key

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

The price is AED 838
AED 2,112 total
includes taxes & fees
2 Sep - 3 Sep
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Summerland Key Hotel Reviews