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Compare 357 Vacation Homes in Summerland Key with updated reviews, rates, and availability.

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

8.8 out of 10, Excellent, (144)
"After reading the other reviews I packed my air mattresses… didn’t need them the beds were fine. The patio rail is fixed based on a previous post. Only 1 working TV but not a big deal. 2 built in ovens but neither works, not ideal for larger family to use a small toaster oven. The place was clean and you can’t beat the location. "
The price is SAR 1,126
SAR 2,352 total
includes taxes & fees
25 Apr - 26 Apr
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (137)
"Nice location. Comfortable place although the couch and living room chair were old and stained. "
The price is SAR 1,032
SAR 2,261 total
includes taxes & fees
20 Apr - 21 Apr
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very Good, (88)
"We stayed for my husband’s surprise 40th birthday weekend. Kazi was an amazing host and made the booking/arrival/departure process so easy. His hospitality was amazing and we can’t wait to come back."
Private Secluded Ocean View & Pool Near Key West

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.6 out of 10, Exceptional, (32)
"Property exceeded expectations, and the view was spectacular! Absolutely would recommend staying here. It has everything you need for a comfy stay. "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (72)
"Beautiful place, thank you for everything. The six of us fit comfortably in this Florida Keys getaway with the best sunrises around. *note* As we were driving out of the keys there was a major fire along the only highway out, Highway 1. The fire consumed over 26,000 acres of land and closed the highway down. The owner of this property not only told us that we could return for the night but she waved the fee. What an astounding gesture,! This is exactly the kind of business owner I would always...
Old Florida Style, wrap around porch, boat basin for dockage, open water

One of the very few beach houses with a daily, rental license in the Keys.

8.8 out of 10, Excellent, (59)
"The house is special, it transmits a lot of peace next to that spectacular dock where the fishing is fabulous, everything is very clean and well equipped with cauldrons etc.I will be back 100%"
The price is SAR 2,249
SAR 5,223 total
includes taxes & fees
22 Apr - 23 Apr
One of the very few beach houses with a daily, rental license in the Keys.

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very Good, (105)
"Definitely need to update the property. Day to day cleanliness was good but many burnt out light bulbs or mismatched bulbs. A coat of paint and updated furniture would help. House A has no view of the water and may have chosen a different place in the complex if i had known. Pool was well taken care of and lots of privacy by the home. Convenient to Key west and lots of good local restaurant choices. Beds were very comfortable. "
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

9.8 out of 10, Exceptional, (215)
"We truly enjoyed our 5 day stay at this rental. The pool on site was super clean and warm. Our granddaughter loved it! We especially enjoyed riding their bikes around the neighborhood. We met many nice neighbors who gave us great tips on beaches, restaurants and other things to do in the area. Highly recommend this as the perfect Keys getaway!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

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

8.6 out of 10, Excellent, (80)
"The house was good for the five of us men. We were comfortable with the sleeping conditions. The kitchen lacked a couple essential pots and dishes to cook with. Yes the house could use some TLC but it was fine for what we needed. I would stay again "
The price is SAR 1,220
SAR 2,733 total
includes taxes & fees
5 May - 6 May
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Relax by Florida Keys Beaches, just a 7-min drive away

9.8 out of 10, Exceptional, (190)
"30 minutes to Key West; great local restaurants (highly recommend the Square Grouper) and within minutes of biking/walking trails. A wonderful location and a well appointed house. We loved it!"
Relax by Florida Keys Beaches, just a 7-min drive away

Mahi House #440 - 35' seawall

The price is SAR 1,290
SAR 2,706 total
includes taxes & fees
19 Apr - 20 Apr
Mahi House #440 - 35' seawall

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

9.8 out of 10, Exceptional, (116)
"We loved having our own space for a boat. Great location."
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

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

9.0 out of 10, Wonderful, (2)
"The property was extremely clean. It was a nice location easy to get to everything we wanted to do. The only thing we found lacking was a king bed was in the listing turned out. It was a trundle bed with king sheets. That was very disappointing as it is not comfortable for two adult adults to sleep on a trundle bed together Ended up using the second bedroom to sleep."
The price is SAR 995
SAR 2,306 total
includes taxes & fees
21 Apr - 22 Apr
Reel Island Retreat #273 at Venture Out in the Florida Keys

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

9.6 out of 10, Exceptional, (89)
"Good location if you need a home base for visiting different locations. Close to Key West, Marathon and Bahia Honda State Park. Small issue with registration as their credit machine was not working but luckily we had cash (this was not property owners fault). It had a funky smell when we first arrived but was better after opening the windows."
The price is SAR 935
SAR 2,089 total
includes taxes & fees
27 Apr - 28 Apr
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

9.6 out of 10, Exceptional, (64)
"Perfect property for a week away. Plenty to keep everyone happy."
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

10.0 out of 10, Exceptional, (221)
"We had a wonderful time kayaking and walking the path across the street. We really enjoyed the home base close enough to Key West to access it when we wanted, but far enough away to stay away from the chaos. The house was just a great home base - clean and really nicely laid out."
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

Sunny Gens - Venture Out #606

6.0 out of 10, (1)
Sunny Gens - Venture Out #606

**KEYSIE DOES IT @ CUDJOE KEY** Private Home in Waterfront Community + LAST KEY

9.2 out of 10, Wonderful, (12)
"Very much enjoyed, Keyes does it."
**KEYSIE DOES IT @ CUDJOE KEY** Private Home in Waterfront Community + LAST KEY

Sailfish Haven #390 - Ocean Views, 35' seawall

8.0 out of 10, Very Good, (4)
"We really enjoyed our stay. The home was exactly as advertised which we definitely appreciated. It was nice to have the kitchen with a wine opener and decent dishes. Being on the water was a plus for our cousin specifically but enjoyed by all. We sat on the back deck morning and night. It was fun to watch the pelicans and boats. Definitely highly recommend. "
The price is SAR 995
SAR 2,306 total
includes taxes & fees
15 Apr - 16 Apr
Sailfish Haven #390 - Ocean Views, 35' seawall
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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Other property types in Summerland Key

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (174)
"My husband and I enjoyed the peacefulness of the area, the beautiful view, the prime location for great places to eat and things to do, the short drive to Key West and Bahia Honda. The cottage was clean, the bed comfy and all was as described. Susan was quick in responding to any questions we had. We will stay here again, I’m sure. "
The price is SAR 845
SAR 1,549 total
includes taxes & fees
21 Apr - 22 Apr
Direct Oceanfront Cottage-Sunrise View- #2,

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (133)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (136)
"Very nice"
The price is SAR 657
SAR 1,297 total
includes taxes & fees
17 Apr - 18 Apr
Cottage with Pool and Dockage, just minutes to 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.