
House holiday rentals in Summerland Key
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Top-rated house rentals in Summerland Key
Guests agree: These houses are highly rated for location, cleanliness and more.
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Popular amenities for Summerland Key house rentals
House rentals with a pool

Keys getaway
We were there to celebrate my husband's 50th birthday. The master bed, pillows and linens were very comfortable. The screened in porch with plenty of comfortable seating was our favorite amenity of the property. We hope to rent there again when we are back in the area. Very comfortable and very clean. 😁

Pelican's Roost, Waterfront comfort at Venture Out
we totally enjoyed our stay. the home is spacious and has everything you would want or need for your stay. loved the screened in porch area! thank you!!!

Moana Hale Paradise #164 - Venture Out, Cudjoe Key
It’s awesome. The additional fees are worth it. The community is great and the commitment to keeping the neighborhood classy is excellent.

Million Dollar View
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.

Ocean Front Home in Great Location
This booking was great for what we needed, thank you to the responsive hosts and pet friendly house that made our vacation that much better.

Sea Turtle Cove
Philip's listing described the place perfectly. Zero unexpected surprises and it had absolutely everything to make our vacation super enjoyable. When it comes to location, so much to do in under 30 minutes. Smack dab in the middle when it comes to driving to Marathon or Key West. It was also great to be able to keep a boat right outside and to have a marina as part of the park. Access to great places to fish are 15-30 minutes away.

Endless Summer
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.

Newely Renovated 3/2-private pool/dock/cabana club
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!
Weekly house rentals

Florida Keys Oceanside Utopia
Shane and Kelly were fabulous! My husband and I enjoyed a week away and loved exploring Marathon. Fishing from the back deck was so much fun. We caught some mangrove snapper that we made for dinner which was exquisite! I also caught a Jack Cravalle and my hubby caught a shark. Definitely fun times! Explored beaches, hiked and went to Key West for a day. Weather did not disappoint. Highly recommend this great vacation home!

Waterfront with Boat Lift/Kayaks and Hot Tub
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!

Discount Available! 100' Dock, Lots of Amenities!
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.

Vaca Vista 3
What a wonderful place to vacation. My entire family had a fabulous time. A bonus was seeing the manatees in the canal. The home was very clean and was very spacious. We all highly recommend this home!!

Movie Theater | HotTub | Pool | Boat/RV/EV Parking
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.

Viamarhe House-Private beach, Kayak, yard games
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

Gorgeous Ocean View Home!
The pictures of this house, while gorgeous, do not do it justice. Not only was the house immaculate and spacious, it has the most stunning view. It is very close to shops and local beaches, and it's centered in between Key West and Islamorada. Yery, our host, was also very helpful and proactive with the one and only challenge we faced. I really can't say enough about this rental. It was spacious enough and contained all the amenities my family of seven could possibly need, including space for our dog. It has the most amazing view of the turquoise water of the Keys. It quite literally checks every box for a checklist of paradise, and I can't wait to go back!

Keysgetaway Retreat. Fish#Fun#Relax
It was a great place. She was on top of things. Water went out not just at her place the whole keys because of main break. She was on top of it went we let her know of the problem and she found out the problem and got back to us.
Private house rentals

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys
Sandra’s conch cottage was comfortable and beautiful and very clean. Provided all the necessary items for the week. The location of the house in Marathon is perfect to all amenities. I would definitely come again.

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ
The place was perfect for our needs. Pool, tiki hut, and canal were great. The beds were comfy as well. Daileny was quick to respond and accommodating.

Sombrero beach oasis, great location, many amenities
Incredible for a family vacation. 🏝️The property feels very private, clean, well decorated, and many amenities. We tried out the paddle boards and spent a lot of time in the pool. When going to the beach, Aileen already had chairs and towels to bring! This property really is a gem. Thank you Aileen!

*Newly Renovated Single Family Home w/Private Pool
Our family had a phenomenal time at this Airbnb. 10/10 recommend, host was fast at communicating and very helpful. Hoping to come back!!!

Waterfront Private Home w/Pool-Family&Pet Friendly
The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club
Beautiful, well appointed home in the middle of the keys within driving distance to all the tourist attractions and restaurants. We are a 3 generation trip with grandparents and kids, and this house had it all! 3 bedrooms, each with excellent ocean views, great kitchen, kayaks and bikes in the garage, and incredible outdoor seating area! Highly recommended for families.

“La casa azul” step 3’ to a private pool
We spent an amazing week in this home. Very comfortable and quiet. The pool was amazing. Will definitely be back.

P31 - 11785 5th Ave. Ocean
I knew that I was limited on what I could do during the week stay bc of a knee injury and it was just fine bc I was quite happy just being at the house for most of my stay. Just loved it and didn’t want to leave. Even though this is an active boating location and boating route l, I still felt quite peaceful staying there. The pool was great and the hot tub was quite beneficial for my knee. Just be careful climbing into the pool. The ladder going up is quite steep. I would’ve preferred some true stairs. But that’s coming from someone with a hurt knee too so take it with a grain of salt. And if you don’t feel like going out to eat, seriously order the steamed shrimp by the pound at FishTails on the corner. It is within walking distance. Will definitely be back for another stay in the future.
Quick stats about house rentals in Summerland Key
Total rentals
210 properties
Nightly prices starting at
$67 NZD before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
150 properties have a pool
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