Search Vacation Homes in Summerland Key

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 280 Vacation Homes in Summerland Key with updated reviews, rates, and availability.

Beachside @ Torchview Waterfront Retreat

9.8 out of 10, Exceptional, (37)
"I had a wonderful 3 weeks stay at Beachside@Torchview. I loved the privacy of the house, the gorgeous sunset views, and the peaceful mornings sitting out on the deck while drinking my morning coffee. I would highly recommend this house for anyone looking for a quiet getaway in the busy Florida Keys. It was everything I had hoped for, and I will definitely be staying here again if I decide to return to the Keys next year. The house was very clean and suited my needs perfectly, and the host...
Beachside @ Torchview Waterfront Retreat

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

9.8 out of 10, Exceptional, (58)
"Our family of five adults and a dog had a fantastic week at this beautiful house! We had plenty of space, it was super clean and well kept. The countertop ice maker was definitely appreciated! We didn’t cook but all the tools you could need are there. We did place an Instacart order from Publix for a few things and delivery was no problem. Lots of restaurants are within a short drive and Kiki’s right down the road was a plus and had great food. We spent most mornings and evenings hanging out on...
Old Florida Style, wrap around porch, boat basin for dockage, open water

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (219)
"Perfect location with sunset views and kayaking "
The price is SAR 1,127
SAR 2,794 total
includes taxes & fees
7 Jan - 8 January 2025
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very Good, (18)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!

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

9.4 out of 10, Exceptional, (28)
"Super nice place Comfortable Couch Comfortable Bed"
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

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

8.4 out of 10, Very Good, (96)
"This place was nice and came as advertised. Location is solid and near a few good restaurants and bars. It could have been a little cleaner but overall was in good shape. Would stay again. Price is good for what you get. "
The price is SAR 845
SAR 2,025 total
includes taxes & fees
23 Dec - 24 Dec
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, (199)
"The Property was as advertised. Great location, had everything we needed, served as both a fantastic base camp between outings and home base. We were able to experience everything we wanted for Thanksgiving as well as hit all the Florida Key highlights (Key West, Bahia Honda , and Piegon Key to list a few), the Venture Out location amenities and activities were a fantastic fit for us as well. Would 100% come back and we are even looking for future dates already. "
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

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

9.8 out of 10, Exceptional, (182)
"We enjoyed our visit to Cudjoe Key. We rented a boat for two days to enjoy snorkeling. It was great being able to tie up the boat outside our rental."
Relax by Florida Keys Beaches, just a 7-min drive away

Fandango - private pool

9.8 out of 10, Exceptional, (76)
"All 8 of us were completely satisfied - no complaints from anyone. We cannot stress enough how spotless this house was - inside and out. Kudos for a wonderful cleaning crew. The online description was accurate, loved the video showing the house and outside surroundings. The decor was lovely, no complaints on the beds. All outdoor furniture was clean and free from any breaks and rust. Hot tub and pool were in working condition and clean. All instructions for use were labeled and visible. The...
Fandango - private pool

Island Therapy

9.8 out of 10, Exceptional, (48)
"We enjoyed everything about this rental. Perfect location. Just beautiful."
Island Therapy

Waterfront Captain House with Boat Basin & Ramp!

9.8 out of 10, Exceptional, (7)
"We had our immediate family together for the first time in 6 months we had the best time together The location and house was amazing "
Waterfront Captain House with Boat Basin & Ramp!

Ocean Front - Private 56' Dock

9.8 out of 10, Exceptional, (135)
"We are experienced Florida renters and we were blown away by this unit. The view alone is worth the stay but we found Venture Out to be absolutely charming. Clean, comfortable, safe, kitchen is well stocked. We will be back for sure!"
The price is SAR 1,155
SAR 3,077 total
includes taxes & fees
5 Jan - 6 January 2025
Ocean Front - Private 56' Dock

44ft Seawall at Sportsman's Paradise

9.4 out of 10, Exceptional, (17)
"Beautiful home for our family & friends weekend at Venture Out. Would love to stay here again for our next trip"
44ft Seawall at Sportsman's Paradise

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.4 out of 10, Exceptional, (45)
"The property is perfect for a couple maybe 3. Its on the smaller side but we loved our time there. Property owner was very attentive even went and bought fishing poles when we asked if there were some available! We will be back!"
20 MINUTES TO KEY WEST , BOATERS PARADISE

Amazing Open Water Views - Venture Out Unit #374

10.0 out of 10, Exceptional, (12)
"This property is as listed. It was clean and the views are great. The location is also good as it is not far from Key West. I rated cleanliness as 4 stars because there was a small ant problem in the unit, lots of traps set up but they were on the kitchen floor. Also, no toiletries were provided such as shampoo and body wash and although the kitchen was well stocked with all things needed for cooking, there were no basics such as salt and pepper or cooking oil and any soaps provided were of...
Amazing Open Water Views - Venture Out Unit #374

Grand Opening! New Construction in Venture Out! 3 night minimum stay.

10.0 out of 10, Exceptional, (1)
"We stayed 4 nights. This unit was much nicer than the pictures show. Essentially everything was immaculate and brand new. The resort was also much nicer than we expected. Would definitely stay again!"
Grand Opening! New Construction in Venture Out! 3 night minimum stay.

Dickey's Dockside Retreat

10.0 out of 10, Exceptional, (1)
"What a way to check out of the weather up north and check into paradise - that's exactly what we did. We'll be back next year."
Dickey's Dockside Retreat

Southern Exposure in Cudjoe Key #49

2.0 star property
Southern Exposure in Cudjoe Key #49

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (186)
"We picked this place for the view and it didnt disappoint. We brought our electric bikes and used them pretty much everywhere. "
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

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

9.8 out of 10, Exceptional, (232)
"The unit was spotless and perhaps one of the best equipped places we have stayed at with VRBO. Everything worked, the utensil drawers were overflowing, extra towels and bedding were provided. There was even a printer available. There were 6 bicycles to pick from and several kayaks (although it was too windy to use this time). Everything in the description is accurate. 5 of 5 rating."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
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.
Don't see what you're looking for?
See all available properties in Summerland Key
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Summerland Key

Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor

2.0 star property
The price is SAR 259
SAR 494 total
includes taxes & fees
2 Jan - 3 January 2025
Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (39)
"The cottage was clean and well appointed. Loved the little porch to sit in late in the evening or drink coffee in early in the morning. Beds were comfy, shower was not as strong as I like (but I'm spoiled by my home one, so . . . ) Only problem we noted was sometimes the toilet would not refill after flushing - simple fix, but kind of annoying. Pool was much smaller than it looked in the picture, though. Really enjoyed our stay and would not hesitate to stay again!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

9.8 out of 10, Exceptional, (58)
"Our family of five adults and a dog had a fantastic week at this beautiful house! We had plenty of space, it was super clean and well kept. The countertop ice maker was definitely appreciated! We didn’t cook but all the tools you could need are there. We did place an Instacart order from Publix for a few things and delivery was no problem. Lots of restaurants are within a short drive and Kiki’s right down the road was a plus and had great food. We spent most mornings and evenings hanging out on...
Old Florida Style, wrap around porch, boat basin for dockage, open water
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.