Holiday Rentals in Summerland Key

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Holiday Rentals in Summerland Key

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.0 out of 10, Wonderful, (184)
"Loved this ocean view property! Very nice location and very comfortable home!"
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Kelly's Kabin - Adorable Private Summerland Key Cottage
9.8 out of 10, Exceptional, (104)
"Check in was super easy.Over all was a very comfortable place.Air condition was nice and cold..Everything worked properly.Located just South of Boondocks Bar&Grille which os one of our favorite spots.Easy to get back and forth to Key West.Would definately stay here again."
The price is €588
includes taxes & fees
1 Dec - 2 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (216)
"Property was clean and had everything to have an enjoyable stay."
The price is €697
includes taxes & fees
23 Nov - 24 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (198)
"The location was perfect and the unit was clean and comfortable. The key lime pie from the hosts was a nice touch."
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Springs Venture Out Dolphin House (#386) with beautiful open water views
9.4 out of 10, Exceptional, (85)
"The accommodations were well above and beyond expectations 💕 The host was easily accessible and very helpful. The place was clean and well stocked. We had an amazing time "
Springs Venture Out Dolphin House (#386) with beautiful open water views
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (95)
"Great property. Brought our boat and had a great time. Quick drive to Key Wedt."
The price is €518
includes taxes & fees
22 Dec - 23 Dec
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.4 out of 10, Exceptional, (26)
"Super nice place Comfortable Couch Comfortable Bed"
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, (57)
"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
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, (54)
"Our trip was supposed to be a boys fishing trip but that was derailed by the hurricane. We were not able to reschedule the trip so my wife and I decided to come down for a private retreat. The house is much more than two people need but we had a great time. The morning views are spectacular. The only thing I would change would be the addition of a full size oven for those who like to cook at the house. "
The price is €1,280
includes taxes & fees
26 Nov - 27 Nov
One of the very few beach houses with a daily, rental license in the Keys.
waterfront cottage near key west, sleeps 6
9.4 out of 10, Exceptional, (16)
"We had a great stay! Other than the weather, everything was perfect! We had plans to dock our boat up at the house but it was too windy to take the boat out. We still enjoyed the patio and grilled out one night! We took showers across the street at the camp restrooms bc there were four of us and we would’ve ran out of hot water but that was no problem. We enjoyed our stay!"
waterfront cottage near key west, sleeps 6
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
Enjoy Caribbean weather in the USA. Openings now through Dec 2024!! Book now!
9.4 out of 10, Exceptional, (133)
"Great location! Fabulous pool! Well be back again for sure ! "
Enjoy Caribbean weather in the USA. Openings now through Dec 2024!! Book now!
Waterfront Cozy Cottage with Boat Ramp & Dock!
10.0 out of 10, Exceptional, (51)
"I really enjoyed it there we / my 12 year old and I . Took out charters everyday that we were there . They will pick you up from your dock ! We will be back .. Great experience!"
Waterfront Cozy Cottage with Boat Ramp & Dock!
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
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
10.0 out of 10, Exceptional, (206)
"Great place!"
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (53)
"The grounds are good. The pools were clean and plenty of deck and dock space. The cottage itself needs help. It needed general maintenance on it. It needs caulking in the bathroom. It needs weather strips around door as it is not tight. There was not enough hand towels and there are no oven mitts in the kitchen. The exhaust fan has been taken out. The ceiling fan in one room only works on high. The ac vents and exhaust fan in the bathroom needs cleaning. We were happy about the porch except the...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (62)
"We are old Florida Keys visitors and past residents. We were delighted with the accommodations, pool and view.We are planning our next stay...same time, same place minus the two days of Helene.Will have to make arraignments for a recliner to be delivered for my wifes sleeping and sitting comfort.Our first night was Sept 20 not the 19th as indicated in error. We stayed 9 nights.Thanks again for the great stay!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Latitudes - Ocean front with pool
10.0 out of 10, Exceptional, (22)
"Beautiful home located on the water and nearby several great restaurants. Only 25 min to Key West. I would highly recommend this property to anyone searching this area for a vacation rental."
Latitudes - Ocean front with pool
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
9.0 out of 10, Wonderful, (67)
"Very quiet, clean, and overall great experience. I’ve been staying at properties in the Keys for over 20 years and this is one of the best experiences I have had."
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
9.6 out of 10, Exceptional, (40)
"The property was just as it was listed as, very clean and very inviting. We loved that it was so quiet! We will definitely go back again!"
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
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 types of properties in Summerland Key you may be interested in

Parmer's Resort
2.5 star property
8.8 out of 10, Excellent, (1001)
"One of the BEST stays in a hotel/resort I have had in a long time. Absolutely perfect! Both check in and check out hosts were amazing, room was VERY clean and comfortable, grounds were clean, peaceful and the beach on the property gave great views. Any time I come down, this will be my choice for stays!"
The price is €146
includes taxes & fees
3 Dec - 4 Dec
Parmer's Resort
Sugarloaf Key Hotel at KOA Resort
3.0 star property
9.8 out of 10, Exceptional, (268)
"Beautiful Beautiful place "
Sugarloaf Key Hotel at KOA Resort
Looe Key Reef Resort
2.5 star property
7.4 out of 10, Good, (1000)
"Great place to stay in the Keys."
The price is €129
includes taxes & fees
2 Dec - 3 Dec
Looe Key Reef Resort
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.

Frequently asked questions

Can I find holiday rentals in Summerland Key?

Yes, there are holiday rentals close to the most popular sights in Summerland Key, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Summerland Key has to offer?

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes: This highly rated holiday home rental in Summerland Key is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games. Some other top choices in Summerland Key are Old Florida Style, wrap around porch, boat basin for dockage, open water and Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill.

How many holiday rentals are there in Summerland Key?

Choose from 438 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Florida Keys Beaches and Sugarloaf Beach are a couple of lovely local spots to get outside and enjoy nature. Venture Out Keys and Upper Sugarloaf Key are other places to visit while you're in town.

What are holiday rentals like in Summerland Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Summerland Key. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.