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Compare 563 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Oceanfront RV Lot with 40' Seawall
10.0 out of 10, Exceptional, (1)
"Location was PERFECT!! Just as described & we can’t wait to visit Venture Out again in summer 2024!!"
Oceanfront RV Lot with 40' Seawall
SPACIOUS RV IN THE KEYS
10.0 out of 10, Exceptional, (2)
"We started our trip by spending two nights in key west but also wanted to spend in a less populated are to experience the more nature oriented part of the keys. The RV was clean and convenient to the overseas highway and the National Key Deer Refuge. There were no problems with our stay."
The price is $1
$145 total
includes taxes & fees
May 26 - May 27
SPACIOUS RV IN THE KEYS
Bungalows at Sugarloaf Beach - The Hemingway
10.0 out of 10, Exceptional, (3)
"Great place to sit back and relax! Lots of peaceful places to hangout with the family. Awesome to walk out right onto the beach (aside from all the seaweed that floated in). Loved the clear kayak and paddle board! So much sea life. Lagoon pool was the best! Wish we had more days."
The price is $995
$1,742 total
includes taxes & fees
May 30 - May 31
Bungalows at Sugarloaf Beach - The Hemingway
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Bimini Breeze in Cudjoe Key
10.0 out of 10, Exceptional, (2)
"This was a super cute place in a very nice association. I had a lot of fun and felt very safe. It was also conveniently located by many great restaurants, groceries and seafood markets. I look forward to returning!!"
Bimini Breeze in Cudjoe Key
Little Palm Island Resort & Spa - A Noble House Resort
4.5 star property
9.8 out of 10, Exceptional, (42)
"fabulous accommodation and staff...service is superb"
Little Palm Island Resort & Spa - A Noble House Resort
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (165)
"Relaxing and beautiful!"
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
ISLAND PARADISE
9.8 out of 10, Exceptional, (26)
"We wanted a place close to but not in Key West and this was perfect for us. The "resort" was gated so we felt safe. We LOVED the accommodation. Though you can see the water from the home, it was just a short walk to the edge of the bay to watch the sunrise. The home we stayed at was perfect for us. It was clean and updated. We loved sitting in the screened porch with our coffee. There was a nice breeze every day we were there. Our last day was spent relaxing at the pool. I would recommend this...
ISLAND PARADISE
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (180)
"very well stocked and clean, Will be back for sure"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Waterfront Venture Out Home
9.6 out of 10, Exceptional, (9)
"What a wonderful place to stay in while visiting Florida Keys. Love the location and was very homey. Thank you"
Waterfront Venture Out Home
Tropical Island Getaway! - Venture Out #653
9.4 out of 10, Exceptional, (8)
"Outstanding but the shower floor needs a slip mat and the faucet is in need of repair. Other than that everything was fine"
Tropical Island Getaway! - Venture Out #653
Comfortable Waterfront Vacation Rental
9.4 out of 10, Exceptional, (136)
"Right price for location 35 minutes from Key West."
Comfortable Waterfront Vacation Rental
Bungalows at Sugarloaf Beach - The Lighthouse
9.4 out of 10, Exceptional, (6)
"Stop thinking about it and BOOK this stay!! Absolutely the best place I stayed out all round, the bungalow was adorable, clean and stocked. The communication was quick and friendly. The little resort was perfect, beautiful and breathtaking! My boyfriend and I stayed for a 3 day romantic getaway and I am already excited to go back again and rent a bigger unit to take the kids. Not one bad thing everything was perfect! I'll say it again stop looking and comparing and just BOOK IT!!"
Bungalows at Sugarloaf Beach - The Lighthouse
Cozy, Perfect Conch Cottage!
9.2 out of 10, Wonderful, (29)
"Our stay was great! The description is accurate. We enjoyed our 6 Mid-March days at "Cozy Perfect Conch Cottage." Yes, it's technically camping, but it's very NICE camping...in a campground...but a very NICE campground. The bed we used (there were only 2 of us) was super comfortable. The WiFi worked great. It was awesome having a full kitchen and washer/dryer. The towels were plentiful, soft and luxurious. Linens were also very soft and comfortable. Everything needed for basic cooking was...
Cozy, Perfect Conch Cottage!
SEA SHELL COTTAGE UNIT #2
9.2 out of 10, Wonderful, (7)
"Nice, quiet, relaxing, reasonably priced with a lovely pool outside our door!"
SEA SHELL COTTAGE UNIT #2
Cheerful Tiny House on 30 min from Key
9.2 out of 10, Wonderful, (16)
"My son and I were coming down to the Keyes for a short vacation, he has just lost his mother and my wife, so I was looking for a place that was accessible, affordable, well maintained, this was the place. Don’t be alarmed at driving into a park, everything was functional and awesome. The hosts were also awesome."
The price is $167
$338 total
includes taxes & fees
May 6 - May 7
Cheerful Tiny House on 30 min from Key
Blue Lobster Lodge - Venture Out #543
9.0 out of 10, Wonderful, (6)
"We had a great stay in this delightful community. Our cottage was clean and very well equipped. We had one problem was immediately addressed and fixed. I highly recommend this property for your vacation!"
Blue Lobster Lodge - Venture Out #543
Parmer's Resort
2.5 star property
8.8 out of 10, Excellent, (1000)
"This is a nice little group of older buildings right on Little Torch Key. Not too fancy but you have a pool, some little piers and even a boat launch. This is not ocean it's water between keys so no surf and mostly coral but a little sand on their beach for getting feet wet. Staff is friendly, they have laundry and a nice little continental breakfast with fresh fruit. Great location for seeing other keys (26 mi to key west) If you really want a beach just 5 miles to one at a state partk and nice...
The price is $147
$199 total
includes taxes & fees
May 16 - May 17
Parmer's Resort
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (123)
"If you like fishing, boating, and swimming, this is the place for you. The property is very safe and quiet. The staff was very friendly and accommodating. Would highly recommend staying here when staying in the Florida Keys. "
Sunshine Key RV Resort & Marina
3 night minimum! Spectacular Ocean Views!
8.8 out of 10, Excellent, (13)
"Unit was slightly smaller than what we were expecting by the pictures. Very clean, except for the floor in main area. Walking around left the soles of your feet very dirty. Used mop that was provided and it cleaned up nicely. When roll-out bed was out, there was no room to maneuver in the room. Everything worked as expected. Neighborhood was quiet and nice. Manager was responsive and very helpful. A lot of amenities were provided and appreciated."
3 night minimum! Spectacular Ocean Views!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (34)
"This property is super cute. Convenient for being close to Key West without the price of Key West. We VERY much enjoyed our 3 night stay. Our property (#15) had a little grill outside so we were able to cookout one night of our stay. Make sure you stop at Publix or Winn Dixie before getting there it is a litle trek to get to grocery store. I would also suggest bringing a few extra bath towels, our cottage only had 3 and 4 adults. Most things you would need, pots, pans, silverware, cups, coffee...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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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.

Where to stay in Summerland Key

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Summerland Key Travel Info

Number of reviews
3,127
Accommodation
563 hotels
Highest price
$995
Lowest price
$1
Reasons to visit
Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market

Frequently asked questions

What's the best place to stay in Summerland Key?

Sugarloaf Key Hotel at KOA Resort is a favorite property for Expedia customers. This hotel offers a marina and a private beach. Reviews from our site also recommend Parmer's Resort and Sugar Loaf Lodge as top options for your visit. See all available top hotels, or vacation rentals in Summerland Key.

What are some of the best vacation rentals in Summerland Key?

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes: Visitors like this Summerland Key vacation home rental. It is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games. Other favorite homes for rent in Summerland Key are Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West and Old Florida Style, wrap around porch, boat basin for dockage, open water. See all vacation rentals in Summerland Key.

If I need to cancel my hotel reservation in Summerland Key, will I receive a refund?

Yes! The majority of hotel bookings are fully refundable if cancelled before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Summerland Key.

Where can I learn more about changing or cancelling my trip to Summerland Key?

For additional details about updating your trip to Summerland Key or cancelling it, click here.

What's the best hotel for a romantic getaway to Summerland Key?

Little Palm Island Resort & Spa - A Noble House Resort is a favorite resort for couples, and features jetted bathtubs and a full-service spa. See all romantic hotels in Summerland Key.

What's the best LGBTQ-friendly hotel in Summerland Key?

Little Palm Island Resort & Spa - A Noble House Resort is a top LGBTQ-friendly resort that features a marina and a full-service spa. See all available hotels listed as LGBTQ-friendly in Summerland Key.

What's the best pet-friendly accommodation in Summerland Key?

Sugarloaf Key Hotel at KOA Resort is a top hotel for people traveling with their pets, and offers a private beach and in-room kitchenettes for its human guests. Other good choices to stay with your pet include Looe Key Reef Resort and Parmer's Resort. See more pet-friendly hotel accommodations in Summerland Key.

Where is the best hotel to stay with easy access to Reel Deal Fishing Charters?

Looe Key Reef Resort is one of the top choices for your stay based on our traveler data, and this hotel offers a restaurant and an outdoor pool. It's located 2.5 mi (4 km) from Reel Deal Fishing Charters. Other good options within 5 miles include Oceanfront Million $$ View and Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West.

What about the best place to stay close to MiLo Watersports?

One of the top choices for your stay is Looe Key Reef Resort, located 2.4 mi (3.8 km) from MiLo Watersports, and this hotel offers a restaurant and an outdoor pool. Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West and Bo's Tropical Get-away- 3yaks,1 Paddleboard,4bikes, Fastwifi, Hbo, Starz,sho&max are other good choices within a few miles.

What's the best hotel for a beach vacation in Summerland Key?

Little Palm Island Resort & Spa - A Noble House Resort is a top resort located on the beach. Parmer's Resort is another good option for your beach trip. See more stays near the beach in Summerland Key.

What are some accommodations with pools in Summerland Key?

ISLAND PARADISE is a top resort with a communal pool, free WiFi, and an in-room kitchen. A couple of other options that offer an onsite pool include RV resort site/rvsite/spot/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT 25% and Luxury Rv lot with access to all the Resorts amenities! . View all hotels with pools in Summerland Key.

What is the best spa hotel in Summerland Key?

Little Palm Island Resort & Spa - A Noble House Resort is a top beachfront spa hotel featuring a fitness center, a hair salon, a bar, and an outdoor pool. Spend an afternoon at Spa Terre where you’ll find facials, body scrubs, and Swedish massages and more. See all spa hotels in Summerland Key.

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