The Best All-inclusive Hotel in Summerland Key, FL from AED 363 in 2026

A coastal pier extending into the sea, surrounded by rocky shores and greenery.

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Recommended hotels in Summerland Key

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

1. Parmer's Resort

Summerland Key

AED 748 total

includes taxes & fees

1 Dec - 2 Dec

A waterfront building with a flat roof, large windows, and a balcony.

2. Sugar Loaf Lodge

Summerland Key

AED 409 total

includes taxes & fees

30 Nov - 1 Dec

A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

3. Looe Key Reef Resort

Summerland Key

AED 682 total

includes taxes & fees

20 Nov - 21 Nov

A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

4. Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key

AED 1,757 total

includes taxes & fees

14 Nov - 15 Nov

5. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Cudjoe Key

AED 1,528 total

includes taxes & fees

13 Nov - 14 Nov

6. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Cudjoe Key

AED 1,742 total

includes taxes & fees

13 Nov - 14 Nov

A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

7. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Cudjoe Key

AED 1,404 total

includes taxes & fees

20 Nov - 21 Nov

A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

8. SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

AED 1,576 total

includes taxes & fees

21 Nov - 22 Nov

9. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Cudjoe Key

AED 1,594 total

includes taxes & fees

13 Nov - 14 Nov

10. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

Cudjoe Key

AED 1,843 total

includes taxes & fees

13 Nov - 14 Nov

View all properties

Choose what matters most at all-inclusive hotels in Summerland Key

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4 stars

Top Summerland Key Hotel Reviews

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

10/10 Excellent

william

A pool area with lounge chairs and a table, surrounded by palm trees.

Orchid Key Inn - Adults Only

Old Town Key West

10/10 Excellent

Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...

Courtney

A tropical outdoor area with palm trees, hanging plants, and string lights.

Douglas House - Adults Only

Old Town Key West

10/10 Excellent

Anthony

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

The Gardens Hotel

Old Town Key West

10/10 Excellent

Anonymous traveler

An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

H2O Suites - Adults Only

Old Town Key West

10/10 Excellent

My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...

Erin

A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

Artist House Key West

Key West Historic District

10/10 Excellent

Anonymous traveler

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

Alexander's Guesthouse - Adult Exclusive

Old Town Key West

10/10 Excellent

Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.

Dominick

A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

Key West Villas

Old Town Key West

10/10 Excellent

Thys

A modern interior with a staircase, a sofa set, a wooden table, and a television.

Simonton Court Historic Inn & Cottages

Key West Historic District

10/10 Excellent

RADANA

A two-story house with a covered porch, a brick pathway, and a large tree.

The Marquesa Hotel

Old Town Key West

10/10 Excellent

David

A porch with a white railing, a bench, and a flag.

The Conch House Heritage Inn

Old Town Key West

10/10 Excellent

Nicholas

A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

Island City House Hotel

Key West Historic District

10/10 Excellent

Keith

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

Duval House

Old Town Key West

10/10 Excellent

The Duval House was absolutely precious. The garden courtyard was beautifully taken care of with plenty of nooks to sit in. The pool is mostly shaded for the hottest part of the day, which seemed especially valuable in comparison to other BnBs. Our room was very comfortable with probably the best bed I’ve been in at a hotel or BnB. And all of the staff was very responsive, friendly, and helpful. Even KissKiss, the property cat, made the rounds to our room to make sure everything was in perfect...

Sarah

A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

The Grand Guesthouse

Old Town Key West

10/10 Excellent

The Grand Guesthouse is a gem in Key West! The host was outstanding and the facility was lovely. Breakfast was simple but nice, and the Happy Hour was an added bonus. We had a nice suite- a bedroom and a living/kitchen area. The room was nicely appointed and it was straightened by the staff each day. The room was very clean! Overall, my wife and I were impressed! Two small improvements... the mattress was too firm. Also, the wifi was not strong enough in our room to stream anything. ...

Anonymous traveler

A pool area with lounge chairs and palm trees.

Santa Maria Suites

Old Town Key West

10/10 Excellent

We stayed here for one night for my husband's 40th birthday. The hotel was aware we were celebrating an occasion and offered complimentary refreshment's in our room. We were able to check on early, got upgraded to pool view and also checked out late! When we arrived we were amazed with how huge the suite was. It was the same size as a condo. The decor was beautiful and the entire place was immaculate, including the outside. What we liked most was how quiet and relaxing the place was (there...

Val

Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

Hyatt Vacation Club at Beach House, Key West

Key West

10/10 Excellent

Sonia

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

Hyatt Vacation Club at Windward Pointe, Key West

Key West

10/10 Excellent

Lindsay

Frequently Asked Questions

Looking for Summerland Key all-inclusive resorts?

Summerland Key offers a host of things to see and do such as Florida Keys Beaches and Upper Sugarloaf Key. Browse our choice of all-inclusive hotels where you can enjoy a host of amenities including entertainment, kid's clubs, and of course food and beverages all included in your stay. Many of our all-inclusive hotel accommodations also feature activities such as golf, yoga, water sports, and more, which you can enjoy without any additional expense.

What is there to do near my all-inclusive resort in Summerland Key?

If you want to explore the area around your all-inclusive resort, visit Florida Keys Beaches and Upper Sugarloaf Key and see why travelers like Summerland Key! Other attractions include Venture Out Keys, Upper Sugarloaf Sound, and Sugarloaf Beach.

When's the best time for an all-inclusive stay in Summerland Key?

There's nothing like an all-inclusive vacation in Summerland Key to refresh you, especially when you know what to expect from the elements. Here's some info to help you choose when to book: The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. March and February are the driest months while September and October are the rainiest months.

Find All-inclusive Resorts in Summerland Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Summerland Key

1. Parmer's Resort

2. Sugar Loaf Lodge

3. Looe Key Reef Resort

4. Kelly's Kabin - Adorable Private Summerland Key Cottage

5. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

6. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

7. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

8. SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

9. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

10. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

Choose what matters most at all-inclusive hotels in Summerland Key

Top Summerland Key Hotel Reviews

Almond Tree Inn Hotel - Adults Only

10/10 Excellent

Frequently Asked Questions

Looking for Summerland Key all-inclusive resorts?

What is there to do near my all-inclusive resort in Summerland Key?

When's the best time for an all-inclusive stay in Summerland Key?