The 10 best hotels with pools in Summerland Key, US | Booking.com
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Hotels with Pools in Summerland Key

Find the hotels with pools that appeal to you the most

The best hotels with pools in Summerland Key

Check out our selection of great hotels with pools in Summerland Key

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Looe Key Reef Resort and Dive Center

Summerland Key

In the Florida Keys, this Ramrod Key resort features a full-service dive center, an outdoor pool and Tiki Bar. Select rooms include a microwave and small refrigerator.

W
Walter
From
Germany
simple but functional and comfortable
Scored out of 10, guest rating 6.8
Pleasant - What previous guests thought, 382 reviews
Price from
$137
1 night, 2 adults

Parmer's Resort

Little Torch Key (Near Summerland Key)

Facing the beachfront, Parmer's Resort offers 2-star accommodations in Little Torch Key and has an outdoor swimming pool, private beach area and shared lounge.

S
Shraddha
From
India
This place is as beautiful as you could dream of. White sand , palm trees , blue ocean, a serene place . Due to misunderstanding on our side, we had canceled and rebooked a room, causing some issues on the guest list. Instead of causing inconvenience, the staff was extremely courteous and helpful. The entire staff was super kind and welcoming. They are really good at taking care of their guests and making them feel extra special.The cottage was well kept; considering it was old construction, the view was heavenly, and the staff responded very well to customer accommodations. If anybody decides to visit Key West, staying at Parmer's is the way to go. We definitely know we will consider Parmer's as the top pick if ever to visit Key West again. Thank you!
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 440 reviews
Price from
$119
1 night, 2 adults

Island Oasis ~ YOUR Paradise Awaits!

Cudjoe Key (Near Summerland Key)

23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Island Oasis ~ YOUR Paradise Awaits! offers accommodations with access to a hot tub. Guests may go for a swim in the private pool.

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 5 reviews
Price from
$250
1 night, 2 adults

Old Wooden Bridge Resort & Marina

Big Pine Key (Near Summerland Key)

Located in Big Pine Key, 25 miles from Florida Keys Aquarium Encounters and 19 miles from Seven Mile Bridge, Old Wooden Bridge Resort & Marina provides sea views and free WiFi.

N
Nicole
From
United Kingdom
We loved the aqua/boat houses on the water! Comfy beds and spacious living rooms. We booked two of the aqua lodges #3 & #6 for our week long family fishing vacation. It was a huge plus to be able to rent a boat through the Marina and to park it at our boat house. Super easy and convenient. Also a huge plus is they are dog friendly and we got to bring our dog with us! He loved walking around the island and becoming friends with the key deer. They were everywhere and it was so precious to see all the fawns walking about!! We enjoyed the quiet nights since the resort is in more of a residential area away from highway 1. Super dark at night so you can view the beautiful starry skies. We Loved our stay and hope to come back again soon! Fishing right off the bridge to No Name Key was fun as well. But my favorite was watching the sun set from the bridge and watching the sun and moon rise from our boat terrace!!
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 242 reviews
Price from
$107.10
1 night, 2 adults

Sugarloaf Lodge

Sugarloaf Shores (Near Summerland Key)

Located in Key West, Florida, this lodge features an outdoor pool and a tennis court. It is 10 minutes’ drive from Key West International Airport.

A
Anamitra
From
India
Great view rooms that are clean, and comfortable.
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 464 reviews
Price from
$99
1 night, 2 adults

Sugarloaf Key Hotel at KOA Resort

Hotel in Summerland Key

Located in Summerland Key, 20 miles from Ernest Hemingway Home and Museum, Sugarloaf Key Hotel at KOA Resort has accommodations with an outdoor swimming pool, free private parking, a private beach...

C
Caroline
From
United States
We LOVED this stay! Absolutely beautiful apartment, felt brand new. Very roomy and clean. Loved all the amenities on the property, will def return!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 188 reviews

Sugarloaf Key RV Resort & Cottages

Summerland Key

Sugarloaf Key RV Resort & Cottages provides air-conditioned accommodations in Summerland Key. Both free Wifi and parking on-site are accessible at the vacation home free of charge.

J
Jana
From
Germany
The cabin was one block from the best amenities I’ve ever stayed in!! It was absolutely beautiful with a great view, super comfy bed, amazing shower, big TV and wonderful little patio with water view!
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 321 reviews

Pelican's Roost, Waterfront comfort at Venture Out

Cudjoe Key (Near Summerland Key)

Featuring free bikes, Pelican's Roost, Waterfront comfort at Venture Out provides accommodations in Cudjoe Key.

B
Bettinna
From
United States
Location, attention to detail, and soooo many amenities!
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 21 reviews

NAUTILUS...ocean front cottage retreat ~

Cudjoe Key (Near Summerland Key)

Providing a garden, NAUTILUS...ocean front cottage retreat ~ features accommodations in Cudjoe Key.

E
Erin
From
United States
The location and house was amazing! Communication was great! Only suggestion is to update the master bedroom mattress and turn up the heat on the showers water, we like a HOT shower. thank you!
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 18 reviews

OCEANIA... water front cottage retreat ~

Cudjoe Key (Near Summerland Key)

23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, OCEANIA... Water front cottage retreat ~ offers accommodations with access to a sauna and hot tub.

A
Angelo
From
United States
Location was great. Really enjoyed it
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 18 reviews
All hotels with pools in Summerland Key

Looking for a hotel with pools?

"Does it have a pool?" is probably one of the most common booking questions no matter where you're looking to stay. These hotels offer a great way to get some exercise without having to hit the gym on your vacation. Indoor pools let you practice your backstroke come rain or shine, while outdoor options are perfect for relaxing in the sun after swimming a few laps.

Most booked hotels with pools in Summerland Key and surrounding area in the past month

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Save money on pools in Summerland Key and nearby – budget options available

  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 5 reviews

    23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Island Oasis ~ YOUR Paradise Awaits! offers accommodations with access to a hot tub. Guests may go for a swim in the private pool.

  • Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 18 reviews

    Providing a garden, NAUTILUS...ocean front cottage retreat ~ features accommodations in Cudjoe Key.

  • Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 18 reviews

    23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, OCEANIA... Water front cottage retreat ~ offers accommodations with access to a sauna and hot tub.

  • Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 21 reviews

    Featuring free bikes, Pelican's Roost, Waterfront comfort at Venture Out provides accommodations in Cudjoe Key.

  • Dock Holiday

    Cudjoe Key
    Budget options available
    Scored out of 10, guest rating 7.1
    Good - What previous guests thought, 6 reviews

    Dock Holiday offers accommodations in Cudjoe Key, 23 miles from Ernest Hemingway Home and Museum and 23 miles from Duval Street. The vacation home has access to a restaurant.

  • 23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Serenity Now Seaside Escape - Brand New Build! offers accommodations with access to a hot tub.

  • Tree Top Paradise

    Cudjoe Key
    Budget options available
    Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 31 reviews

    23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Tree Top Paradise provides accommodations with access to a spa center.

  • Parrotfish Pointe

    Cudjoe Key
    Budget options available

    Parrotfish Pointe is located in Cudjoe Key, just 24 miles from Ernest Hemingway Home and Museum and 24 miles from Duval Street. This beachfront property offers access to a patio.

Enjoy breakfast in Summerland Key and nearby

  • Foster`s Folly

    Key West
    Breakfast options

    Foster`s Folly is located in Key West, just 30 miles from Duval Street and 30 miles from Southernmost Point. The air-conditioned accommodation is 30 miles from Ernest Hemingway Home and Museum.

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 440 reviews

    Facing the beachfront, Parmer's Resort offers 2-star accommodations in Little Torch Key and has an outdoor swimming pool, private beach area and shared lounge.

    From $183.38 per night
  • Salty Air Retreat offers accommodations in Little Torch Key, 26 miles from Florida Keys Aquarium Encounters and 29 miles from Ernest Hemingway Home and Museum.

  • Blackbeard Retreat is located in Little Torch Key, just 29 miles from Ernest Hemingway Home and Museum and 29 miles from Duval Street.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 4 reviews

    21 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Ocean View with Pool, 4 bedroom Vila Near Key West offers accommodations with access to a fitness room.

    From $758.56 per night
  • Newly built home in Cudjoe Key is located in Cudjoe Key, just 21 miles from Ernest Hemingway Home and Museum and 21 miles from Duval Street. With pool views, this accommodation features a balcony.

  • Beachside Fantasy is located in Big Pine Key, just 23 miles from Florida Keys Aquarium Encounters and 30 miles from Ernest Hemingway Home and Museum.

  • Hellenga Haven offers accommodations in Big Pine Key, 25 miles from Captain Hook S Marina Dive Center and 26 miles from A Deep Blue Dive Center.

Hotels with a pool that guests love in Summerland Key

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  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 reviews
    This is a great place, it's thought of everything- kayaks, bikes, aquacabanas, hammocks, a spacious design between cabins, rvs and sites with surrounding water and wetlands. We were a couple in a beautiful cabin but could see it's great for families too. The pool was a highlight too!
    Guest review by
    annette
    Young couple
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 reviews
    Everything was perfect. Great location, great amenities, pool was warm, kayaks and paddle boards easily accessible. House was spotless and very well maintained. Great dinning and live music across the street!
    Guest review by
    Brett
    Family with young children
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 reviews
    We stayed in one of the bungalows on the property. We loved that it was right on the water & had many amenities to take advantage of, including a pool, kayaks, and the "aquabanas". Our bungalow was new, clean, & very easy to find with the instructions & map provided. Only a 30 min drive to Key West...some may say this is a disadvantage but we loved being able to retreat back to a quieter area in the Keys after being in Key West during the day.
    Guest review by
    Olivia
    Young couple
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 reviews
    The cabin was very clean. Most of the things inside are working well. Our cabin was facing the lake. Very beautiful view when you are up having your coffee in the morning. The pool was nice but we didn’t have time to use it. We used the kayak and we were having fun especially during sunset. The floating cabana was impressive. We wish we have friends to have a party there.
    Guest review by
    Geraldine
    Young couple
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 reviews
    We stayed in one of the cottages. It was very clean, with a nice layout. The amenities were wonderful. There is a big tiki hut for social gathering, as well as a fire pit. We used the pool, kayaks and the "aquabanas" (floating seating with table and covering for shade) and played corn hole. There was live music, also. We were near the pool and the big tiki hut, but it was very quiet at night. The staff was very friendly. The location was great! Only 20 minutes to Key West.
    Guest review by
    Diane
    Young couple
  • Avg. price/night: $154.13
    Scored out of 10, guest rating 6.8
    Pleasant - What previous guests thought, 382 reviews
    Yep. Comfortable room. Nice shower. Very nice pool. We absolutely loved the Tiki bar
    Guest review by
    Sheri
    Young couple
  • Avg. price/night: $154.13
    Scored out of 10, guest rating 6.8
    Pleasant - What previous guests thought, 382 reviews
    The location is very good. The staffing good. Pool, Tiki Hut, food, snorkle & scuba on site.
    Guest review by
    John
    Family with young children
  • Avg. price/night: $154.13
    Scored out of 10, guest rating 6.8
    Pleasant - What previous guests thought, 382 reviews
    The vibrant colours, swimming pool, restaurant (the tiki bar). They offer water adventure activities like scuba diving, snorkelling. Staff is very supportive.
    Guest review by
    Prerana
    Family with young children
  • Avg. price/night: $154.13
    Scored out of 10, guest rating 6.8
    Pleasant - What previous guests thought, 382 reviews
    We had a superb view of the canal in Room 11. We loved the pool and having the Tiki Hut steps away was a bonus. The shower was absolutely the best!
    Guest review by
    Patricia
    Young couple
  • Avg. price/night: $154.13
    Scored out of 10, guest rating 6.8
    Pleasant - What previous guests thought, 382 reviews
    The location, the tiki bar, the pool, the beds and the silence during the night
    Guest review by
    Diego
    Family with young children
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