Book 5 Star Hotels in Summerland Key

Name: Cottage with Pool and Boat Dockage just minutes to Key West!
Price range: $317 total

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Dec 31 - Jan 1

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Jan 1 - Jan 2

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Featured Summerland Key 5 Stars Hotels

Free Cancellation

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2.39 mi from city center

$140 nightly

$158 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

Guests staying at Looe Key Reef Resort enjoy karaoke, an outdoor pool, and free WiFi in public areas. If you drive, put free parking to good use. Front-desk staff can assist with luggage storage and tours/tickets. Additional amenities include express check-in, a vending machine, and a picnic area.

Pool

Pet friendly

Free Cancellation

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3.64 mi from city center

$235 nightly

$265 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

Guests of Parmer's Resort have access to a private beach, a marina, and an outdoor pool. A stay here includes free parking. The front desk has multilingual staff that can help with concierge services and luggage storage. Other amenities at this beach motel include free WiFi in public areas, coffee/tea in a common area, and a microwave in a common area.

On private beach

Pool

Free Cancellation

Reserve now, pay when you stay

7.66 mi from city center

$199 nightly

$224 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Guests staying at Sugar Loaf Lodge enjoy access to a marina, an outdoor pool, and outdoor tennis courts. If you drive, take advantage of free parking. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Additional amenities include free WiFi in public areas, a vending machine, and a garden.

Pool

Parking included

4.59 mi from city center

Guests of Sugarloaf Key Hotel at KOA Resort have access to a private beach, a marina, and an outdoor pool. If you drive, put free parking to good use. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Additional amenities include free WiFi in public areas, a hot tub, and laundry facilities.

On private beach

Pool

3.65 mi from city center

Guests staying at Little Torch Cottages enjoy 2 outdoor pools, a sauna, and free use of bicycles. If you drive, take advantage of free parking. This hotel also has laundry facilities.

Pool

Parking included

3.4 mi from city center

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.

Pool

Kitchen

3.56 mi from city center

At this vacation home, guests enjoy an outdoor pool, a gym, and a hot tub. Additional amenities include laundry facilities, barbecue grills, and a garden.

Pool

Hot Tub

3.36 mi from city center

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

Pool

Kitchen

3.36 mi from city center

$286 nightly

$317 total

Jan 7 - Jan 8, 2026

Total with taxes and fees

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Pool

Kitchen

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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.

Best 5 star hotels in Summerland Key

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Summerland Key. After all, treating yourself to the finer things is what vacations are about.

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Summerland Key hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
Summerland Key 5 star hotels and resorts typically offer luxury amenities such as:

Gourmet restaurant
Full-service fitness center with pool
Luxury spa
Welcome gifts upon arrival
Top-of-the-line beds and linens
Designer personal care products
Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Summerland Key with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place:

Search hotels by price, ranging from $158 to $317
Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
Choose from 616 5 star hotels in Summerland Key!

Summerland Key hotels essential information

Accommodation	616 hotels
Lowest Price	$158
Highest Price	$317
Popular hotels	Looe Key Reef Resort, Parmer's Resort, Sugar Loaf Lodge, Sugarloaf Key Hotel at KOA Resort, Little Torch Cottages, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Private Secluded Ocean View & Pool Near Key West, Cottage with swimming pool and dockage, just minutes to Key West!, Cottage with Pool and Boat Dockage just minutes to Key West!

Recent Reviews

5/5 Excellent

"Appartement très propre (voir neuf) et super bien équipé. Environnement très beau et magnifique piscine et jacuzzi. Personnel sympathique et souriant. "

A verified traveler stayed at Sugarloaf Key Hotel at KOA Resort

Posted 3 days ago