A coastal road with a beach on one side and a marina with boats on the other.

Find hotels in Summerland Key, FL from 2.206.464 ₫

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15 Sep - 16 Sep
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16 Sep - 17 Sep
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18 Sep - 20 Sep
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25 Sep - 27 Sep

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Our top choices for Summerland Key hotels

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.
A dining area with a table and chairs, a ceiling fan, a television, and a window with a view of the outdoors.
A sunset view with a thatched structure and a palm tree by a calm body of water.

1. Parmer's Resort

Parmer's Resort
Summerland Key
United States
Mireya
3.503.088 ₫
4.786.744 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Parmer's Resort
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.
A canal with boats docked on both sides, surrounded by lush greenery and trees.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
United States
Sarah
1.961.302 ₫
2.206.464 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Looe Key Reef Resort
A waterfront building with a flat roof, large windows, and a balcony.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

3. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
United States
Marjorie
3.084.480 ₫
3.470.170 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Sugar Loaf Lodge
A wooden deck with a swing chair overlooking a lush landscape.
A covered outdoor area with a concrete floor, a central table with chairs, and a wooden staircase leading to an upper level.
A two-story house with a balcony and a staircase leading to the upper level.
A modern bathroom with a glass-enclosed shower, a toilet, and a small window.

4. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
Summerland Key
United States
max
6.467.405 ₫
16.758.329 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Starlight Serenity - Hideaway w Stunning Views
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.
A concrete pathway flanked by lush green foliage, leading to a shaded area.
A large house with a pool, surrounded by lush greenery.
A bedroom with a large bed, a ceiling fan, and a balcony with a view of greenery.

5. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
United States
Preetam
13.413.600 ₫
25.296.300 ₫ total
includes taxes & fees
17 Sept - 18 Sept
Atlantic View Luxury Villa with Pool
A swimming pool with clear water, surrounded by lush greenery and palm trees.
A covered porch with white columns and wicker furniture.
A yellow building with a blue door and shutters, a number '302' on the wall, and a small porch area.
A bedroom with a bed, a ceiling fan, an air conditioning unit, a bedside table, a lamp, and a window with blinds.

6. Tranquility Guest House

Tranquility Guest House
Old Town Key West
United States
Sandra
2.117.794 ₫
4.691.047 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Tranquility Guest House
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

7. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
United States
Anais
2.916.000 ₫
4.009.370 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A couple holding hands in a tropical setting with palm trees and greenery.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

8. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Danielle
2.842.128 ₫
4.655.395 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Blue Flamingo Resort Key West
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.
A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.
A two-story building with a central entrance, surrounded by palm trees and a wooden walkway.
A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.

9. Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
Key West
United States
Mauricio
4.750.308 ₫
6.512.972 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Hyatt Vacation Club at Windward Pointe, Key West
A coastal landscape with clear turquoise waters and a dense tree line under a bright blue sky with scattered clouds.
An aerial view of a coastal area with a marina, several boats, and a variety of buildings including a large resort with a pool and landscaped areas.
A coastal area with a marina, boats, and a small island with buildings.
A waterfront dock with boats and a sunset.

10. Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway
Marathon
United States
michael
2.401.488 ₫
3.430.673 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Captain Pips Marina & Hideaway
A poolside area with lounge chairs, a staircase leading to a balcony, and a pool.
A Southernmost Inn with a porch, a sign indicating vacancy, and a staircase leading to the entrance.
A beige sofa with two pillows, flanked by two wooden side tables with lamps and potted plants, against a white wall with a framed picture of a tree.
An outdoor patio with tables and chairs, surrounded by trees and a house.

11. The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only
Old Town Key West
United States
Ron
1.733.831 ₫
3.119.174 ₫ total
includes taxes & fees
16 Sept - 17 Sept
The Southernmost Inn - Adults Only
A balcony with a view of a street, a bench, and a potted plant.
A reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.
A hotel lobby with a bar area, seating, and a fireplace.
A bar area with a Pegasus International Hotel sign, round tables, and metal chairs.

12. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
Canada
Shahid
3.289.733 ₫
5.015.934 ₫ total
includes taxes & fees
18 Sept - 19 Sept
Pegasus International Hotel
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A covered walkway with a wooden ceiling, white railings, and a brick path.
A compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.
A garden with a pond, rocks, and various plants.

13. Island City House Hotel

Island City House Hotel
Key West Historic District
United States
Osvaldo
3.985.200 ₫
4.483.350 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Island City House Hotel
A hotel room with two beds, each with a wooden headboard, white bedding, and a bedside table with a lamp.
A compact living space with a kitchenette, dining area, and seating area.
A dining area with a wooden table and chairs, a chandelier, and a kitchen in the background.
A kitchen with wooden cabinets, a stainless steel refrigerator, a granite countertop, a sink, a microwave, a stove, and a clock.

14. Knight's Key Suites

Knight's Key Suites
Marathon
United States
chantal
1.784.592 ₫
2.564.784 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Knight's Key Suites
A hotel room with a bed, a view of the beach, a hammock, and beach chairs.
A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.
A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.
A pool area with blue lounge chairs, a hot tub, and a covered seating area.

15. Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
United States
Roland
2.783.808 ₫
3.967.963 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Ibis Bay Beach Resort
A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.
A row of bicycles parked in front of a building with a white balcony and a palm tree.
A compact kitchen with white cabinets, a microwave, and a small dining area with two wicker chairs.
A hotel with a white facade, multiple balconies, and lush tropical landscaping.

16. The Palms Hotel

The Palms Hotel
Old Town Key West
United States
Zachary
2.672.258 ₫
3.590.728 ₫ total
includes taxes & fees
28 Sept - 29 Sept
The Palms Hotel
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.
A hotel room with a balcony, a bed, a desk, and two chairs.
A bar area with a thatched roof, wooden chairs, and a poolside view.

17. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
United States
Lois
3.493.118 ₫
3.929.758 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Hampton Inn Key West FL
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.
A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.
A bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.
A row of blue bicycles parked under a tree, with a white fence and a building in the background.

18. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West
United States
Alissa
2.924.164 ₫
3.937.685 ₫ total
includes taxes & fees
16 Sept - 17 Sept
The Grand Guesthouse
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.
A breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.
A two-story house with a white exterior, a green roof, and a staircase leading to the upper floor.

19. Westwinds Inn

Westwinds Inn
Key West Historic District
United States
Tricia
3.013.200 ₫
3.389.849 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Westwinds Inn
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.

20. Eden House

Eden House
Key West Historic District
Canada
Erik
2.663.165 ₫
3.355.587 ₫ total
includes taxes & fees
11 Oct - 12 Oct
Eden House
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Where to stay in Summerland Key

Find the best Summerland Key areas for the activities you enjoy most.
A calm lake with several white birds, including herons and pelicans, on the water's edge.
A beach with dead trees and a calm sea at sunset.

Cutthroat Harbor Estates

Cutthroat Harbour Estates offers a tranquil slice of Florida Keys living with private boat docks and crystal-clear waters. This residential waterfront area provides an authentic escape from tourist crowds. Homes on stilts with weathered wood docks create a classic Keys atmosphere. The neighborhood's canals connect directly to the Gulf, making it perfect for fishing and boating enthusiasts. Gentle waves lap against private docks while tropical birds call at dawn. Nearby Venture Out Keys and Summerland Key provide dining options and additional sights.

A waterfront property with a pool, palm trees, and a building with a white roof.
A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.
A waterfront property with multiple houses, palm trees, and a calm sea.
A boat docked near a waterfront with a house and palm trees in the background.
A waterfront with a pier, calm water, and houses with palm trees in the background.

Sugarloaf Shores

Sugarloaf Shores offers a tranquil escape on the Florida Keys waterfront. Private homes line peaceful canals where turquoise waters invite fishing, kayaking, and boating adventures. This residential haven sits away from tourist crowds yet provides easy access to stunning ocean views. The neighborhood's charm lies in its authentic Keys lifestyle with homes on stilts and tropical landscaping. Nearby Sugarloaf Beach and Lower Sugarloaf Sound provide perfect spots for swimming and snorkelling. Visitors appreciate the quiet streets for evening strolls and stargazing.

An aerial view of a bridge over turquoise water.

Cudjoe Gardens

Cudjoe Gardens offers a peaceful waterfront retreat in the Florida Keys. This quiet residential haven features canal-front properties with private docks for easy boat access. Travellers can enjoy fishing, wildlife watching, and stargazing from their holiday rentals. The neighborhood's tropical charm comes alive with pastel homes on stilts surrounded by palm trees and native plants. A hire car is essential for exploring nearby Summerland Key attractions and dining options. Water enthusiasts will appreciate direct canal access to open waters and nearby beaches.

An aerial view of a long bridge over turquoise waters with a few vehicles on it.

Bay Point

While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.

An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

Escape to the peaceful shores of Breezeswept Beach Estates on Summerland Key. This residential haven offers private waterfront properties with boat docks and direct access to crystal-clear Florida waters. The neighborhood's charm lies in its quiet streets lined with pastel homes and tropical landscaping. Outdoor enthusiasts will love exploring nearby Newfound Harbour Keys by kayak or boat. Fish in the shallow waters, spot native birds, or simply relax under swaying palms. With minimal commercialization and abundant natural beauty, this peaceful retreat captures authentic Keys living without the tourist crowds.

Stay near popular Summerland Key attractions

Sugarloaf Beach

8.4/10 (38 reviews)
This secluded private beach on Sugarloaf Key offers a tranquil escape from the busier Florida Keys shorelines. Guests enjoy pristine views and peaceful sunbathing in a natural, amenity-light setting.
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Upper Sugarloaf Key

8.6/10 (54 reviews)
Upper Sugarloaf Key serves as a gateway to the Great White Heron National Wildlife Refuge with pristine waters. Kayak through mangroves at dawn to spot diverse bird species in this tranquil Florida Keys ecosystem.
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Pye Key

This unspoiled island near Summerland Key offers pristine waters for snorkelling and marine life observation. Bring supplies and reef-safe sun cream for your half-day adventure in this natural Florida Keys sanctuary.
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Upper Sugarloaf Sound

9.2/10 (17 reviews)
Glide through Upper Sugarloaf Sound's tranquil waters surrounded by vibrant mangroves and diverse birdlife. Kayak or paddleboard this peaceful Florida Keys retreat to experience nature at its most serene.
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Venture Key

This private Florida Keys community offers waterfront holiday rentals with direct access to pristine boating waters. Enjoy the heated pool and tennis courts before setting out from the marina for a day of fishing.
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Crab Key

Crab Key is a private residential island off Summerland Key in the Florida Keys with no public access. This exclusive enclave remains one of the few truly private islands in the Keys.
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Squirrel Key

Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.
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Boondocks Grille & Draft House

Boondocks Grille & Draft House is just one of the places to see in Summerland Key, so why not enjoy the other things to explore during your travels?
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Learn more about Summerland Key

Snorkel the vibrant coral reefs at Looe Key, where rangers can direct you to spots with fewer boats. Rent kayaks to explore the mangrove trails, then ask locals about their favourite seafood shacks serving fresh-caught Keys lobster.

See all hotels in Summerland Key
A long bridge over turquoise waters with clear skies.

Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Great resort setting whether camping or in the hotel. I have been staying in the RV sites since they reopened a few years ago and this was my first time staying in the hotel and was very impressed. The staff is always awesome and they have a great marina. Excellent restaurants nearby and the pool, bar, cafe and activities are a big plus."
David 3-night trip
Posted 13 hours ago
Sugarloaf Key Hotel at KOA Resort
Parmer's Resort

Parmer's Resort

10/10 Excellent
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
Mireya 1-night trip
Posted 4 days ago
Parmer's Resort
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"Make sure to meet Lena and get the right place and deal from her"
Harshwardhan 2-night trip
Posted 5 days ago
Sugarloaf Key RV Resort & Cottages

More cheap stays in Summerland Key

Looe Key Reef Resort

Looe Key Reef Resort

27340 Overseas Highway Summerland Key FL
1.961.302 ₫
2.206.464 ₫ total
5 Oct - 6 Oct
includes taxes & fees
Looe Key Reef Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

17001 Overseas Hwy Summerland Key FL
3.084.480 ₫
3.470.170 ₫ total
16 Sept - 17 Sept
includes taxes & fees
Sugar Loaf Lodge
Parmer's Resort

Parmer's Resort

565 Barry Avenue Summerland Key FL
3.503.088 ₫
4.786.744 ₫ total
27 Sept - 28 Sept
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
Parmer's Resort
Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views

Summerland Key FL
6.467.405 ₫
16.758.329 ₫ total
5 Oct - 6 Oct
includes taxes & fees
10/10 Exceptional! (1 review)
Starlight Serenity - Hideaway w Stunning Views
Luxury Oceanview Pool Eco-friendly Villa Near Key West

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key FL
Get ratesLuxury Oceanview Pool Eco-friendly Villa Near Key West
Little Torch Cottages

Little Torch Cottages

28501 Channel View Drive Summerland Key FL
Get rates
8.6/10 Excellent! (10 reviews)
Little Torch Cottages

Hotels in Summerland Key with star rating

Frequently asked questions

What's the seasonal weather in Summerland Key?
The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 23°C. Average annual precipitation for Summerland Key is 895 mm.

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