Summerland Key Vacation Rentals

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Browse Select Summerland Key Vacation Homes

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

10.0 out of 10, Exceptional, (3)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

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

9.0 out of 10, Wonderful, (151)
"The place was spacious, very clean and beautiful!"
The price is CA $379
CA $830 total
includes taxes & fees
Aug 10 - Aug 11
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

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

9.6 out of 10, Exceptional, (77)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is CA $414
CA $962 total
includes taxes & fees
Aug 18 - Aug 19
Old Florida Style, wrap around porch, boat basin for dockage, open water

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (250)
"Home was clean and great location! Would definitely stay here again! "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

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

8.8 out of 10, Excellent, (85)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
The price is CA $434
CA $988 total
includes taxes & fees
Aug 7 - Aug 8
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

9.6 out of 10, Exceptional, (56)
"It was a beautiful home and Francine, our host, was most accommodating."
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.4 out of 10, Exceptional, (57)
"Great little spot, location was perfect, house was cozy, and the host was fantastic! The staff at Venture Out were also extremely courteous. Would definitely stay here again. "
20 MINUTES TO KEY WEST , BOATERS PARADISE

Private Secluded Ocean View & Pool Near Key West

8.2 out of 10, Very good, (93)
"Everything was exactly as described, the host was gracious and communicative, the house is great for a large group and a quiet location"
Private Secluded Ocean View & Pool Near Key West

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

8.4 out of 10, Very good, (114)
"Deer in the front yard, perfect location, clean and friendly "
The price is CA $310
CA $743 total
includes taxes & fees
Aug 13 - Aug 14
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (6)
"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 CA $365
CA $856 total
includes taxes & fees
Aug 19 - Aug 20
Island Time #110 Ocean Views - Cudjoe Key

A Tropical Luxury Getaway, Your own private resort!!

10.0 out of 10, Exceptional, (38)
"The house and pool were very nice."
A Tropical Luxury Getaway, Your own private resort!!

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 CA $336
CA $816 total
includes taxes & fees
Aug 17 - Aug 18
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Private and Exclusive Florida Keys Getaway

10.0 out of 10, Exceptional, (12)
"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"
The price is CA $593
CA $1,374 total
includes taxes & fees
Aug 8 - Aug 9
Private and Exclusive Florida Keys Getaway

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

9.6 out of 10, Exceptional, (40)
"We were on the end of canal with wonderful sunrise.Beds comfortable and the towels were large and plush.Well equipped kitchen for our cooking needs.A well maintained community with a pool, convenience store home to RVs as well as permanent places to stay."
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View

9.8 out of 10, Exceptional, (71)
"Very pleased with this adorable home thank you "
VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View

Lower Keys paradise

10.0 out of 10, Exceptional, (34)
"The property was very clean and comfortable. We had a great stay "
Lower Keys paradise

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

9.6 out of 10, Exceptional, (96)
"Really great, friendly community with lots of activities and a great view of the beach. Would definitely be on my list for another visit soon."
The price is CA $205
CA $601 total
includes taxes & fees
Aug 10 - Aug 11
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Keys House - Venture Out Lot 220

2.5 star property
9.6 out of 10, Exceptional, (5)
"We loved the condo and spent a lot of time on the upper patio enjoying the view. Very clean. Spacious for 4 of us. Felt extremely safe. Thank you very much!!!"
Keys House - Venture Out Lot 220

Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise

9.6 out of 10, Exceptional, (52)
"Great location & great boating access."
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise

Tarpon Alley - Venture Out 509

2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was very clean , very well equipped. Very nice home. Very comfortable inside and out. Wish I was still there ! Would absolutely recommend. "
Tarpon Alley - Venture Out 509
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