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

Summerland Key Hotel Guide - Hotels with Pool in Summerland Key, Florida

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Check availability on Summerland Key Hotels with Pool

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Summerland Key hotels with a pool

A sunset view with a thatched structure and a palm tree by a calm body of water.
A hotel room with a bed, a flat-screen TV, a small kitchenette, and a balcony with a view of palm trees and 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 white building with a covered patio area, surrounded by palm trees and a view of the ocean.

1. Parmer's Resort

Parmer's Resort
Summerland Key
  • Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
€176
includes taxes & fees
3 Nov - 4 Nov
Parmer's Resort
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
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.

2. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
€119
includes taxes & fees
18 Oct - 19 Oct
Sugar Loaf Lodge
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

3. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
€140
includes taxes & fees
26 Oct - 27 Oct
Looe Key Reef Resort
A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.
A marina with RVs docked along a waterway, surrounded by palm trees and buildings.
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.
A waterfront property with a two-story building, a covered outdoor area, and a dock.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
€372
includes taxes & fees
21 Oct - 22 Oct
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a swimming pool, beach area, and marina.
A coastal residential area with houses, a marina, and a flag.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.

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

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
€377
includes taxes & fees
18 Oct - 19 Oct
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Pool
Outdoor dining
Sports court
Beach

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

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
€412
includes taxes & fees
11 Nov - 12 Nov
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A marina with boats, a dock, and a white building with a balcony.
A waterfront property with a covered porch, a boat dock, and a clear sky.
A covered balcony with a table and chairs, a grill, and a boat docked nearby.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

7. SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
€384
includes taxes & fees
19 Oct - 20 Oct
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A beachfront property with a pool, palm trees, and a two-story building.
A waterfront view with a marina, a boat docked, and a building with a balcony.
A residential street with houses, a driveway, and a gravel path.
A beachfront property with a large house, a parked bus, and a rocky foreground.

8. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
€232
includes taxes & fees
18 Oct - 19 Oct
Seabreeze Escape WF RV Lot 489
Pool
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.
Sports court
Beach

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

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
€409
includes taxes & fees
20 Oct - 21 Oct
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A resort with a swimming pool, beach area, and marina.
A coastal residential area with houses, RVs, and a clear view of the ocean.
A beachside area with palm trees, picnic tables, and a view of the sea.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
€473
includes taxes & fees
18 Oct - 19 Oct
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
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Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
4 stars
Hot tub
5 stars
Spa

Hotels with pools and hot tubs in Summerland Key

A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A coastal residential area with houses, a marina, and a flag.
A resort with a swimming pool, beach area, and marina.
A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
€377
includes taxes & fees
18 Oct - 19 Oct
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A waterfront property with a covered porch, a boat dock, and a clear sky.
A marina with boats, a dock, and a white building with a balcony.
A bedroom with a bed, a ceiling fan, a window with blinds, and a door with a sign.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
€384
includes taxes & fees
19 Oct - 20 Oct
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
Outdoor dining
Sports court
Beach

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

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
€412
includes taxes & fees
15 Nov - 16 Nov
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A beachfront property with a pool, palm trees, and a two-story building.
A waterfront view with a marina, a boat docked, and a building with a balcony.
A residential street with houses, a driveway, and a gravel path.
A beachfront property with a large house, a parked bus, and a rocky foreground.

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
€232
includes taxes & fees
18 Oct - 19 Oct
Seabreeze Escape WF RV Lot 489
Pool
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.
Sports court
Beach

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

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
€409
includes taxes & fees
20 Oct - 21 Oct
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
Outdoor dining
A marina with RVs and mobile homes, a swimming pool, and a view of the ocean.
A resort with a swimming pool, beach area, and marina.

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
€443
includes taxes & fees
18 Oct - 19 Oct
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A coastal residential area with houses, RVs, and a clear view of the ocean.
A beachside area with palm trees, picnic tables, and a view of the sea.
A resort with a swimming pool, beach area, and marina.

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

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
€473
includes taxes & fees
18 Oct - 19 Oct
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A playground with various play structures, including a climbing frame and a swing set, surrounded by a fence and palm trees.
A gravel area with a manhole cover, a palm tree, and a building with a balcony.
A swimming pool with palm trees and a view of the sea.
A Silverback RV parked by a dock with a clear blue sky, palm trees, and a thatched umbrella.

Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West

Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West
Cudjoe Key
€135
includes taxes & fees
18 Oct - 19 Oct
Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
Marina
Outdoor dining
Living area

Canal-Front Retreat with Dock, Pool & Open Ocean Views

Canal-Front Retreat with Dock, Pool & Open Ocean Views
Cudjoe Key
€443
includes taxes & fees
29 Oct - 30 Oct
Canal-Front Retreat with Dock, Pool & Open Ocean Views
Pool
A living room with a sofa, armchair, TV, and a view of the outdoors.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
Outdoor dining

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

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
€453
includes taxes & fees
17 Nov - 18 Nov
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
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.
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Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"I've stayed at Parmers several times and anytime I'm in the Keys Parmers is where I stay. Staff is excellent."
Ken 2-night trip
Posted 2 days ago
Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

8/10 Good
"Balcony"
Martin 1-night trip
Posted 3 days ago
Sugar Loaf Lodge
Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"They had a nice pool you could park your boat in the channel they also had a very nice tiki bar and grill it was an ok place to stay but parking sucked"
Todd c 1-night trip
Posted 6 days ago
Looe Key Reef Resort

Frequently asked questions

What's it like visiting Summerland Key?
If taking it easy by the pool is your idea of a great getaway, you may want to look at Summerland Key, which has 27 places to stay with pools. During your visit, you can explore attractions such as Florida Keys Beaches, and then relax and unwind poolside at one of the accommodation options in Summerland Key that travellers like for their pools.
What are some accommodation options with pools in Summerland Key?
Parmer's Resort: Features a private beach, an outdoor pool and daily. Sugarloaf Key Hotel at KOA Resort: Offers a private beach, an outdoor pool and a snack bar/deli. Sugarloaf Key RV Resort & Cottages: Provides a private beach, an outdoor pool and a full-service spa. Looe Key Reef Resort: Features free self parking, an outdoor pool and complimentary wireless Internet access. Sugar Loaf Lodge: Hotel located near Florida Keys Beaches. Offers free self parking, an outdoor pool and complimentary wireless Internet access.
How many hotels with pools can I expect to find in Summerland Key?
Expedia's 27 hotels in Summerland Key give you a great choice for your poolside getaway.
What is there to see and do in Summerland Key?
Explore places such as Florida Keys Beaches while you're in Summerland Key. Spend some time experiencing the great outdoors at Upper Sugarloaf Key and Venture Out Keys.
When is the best time to book a hotel with a pool in Summerland Key?
Taking the local weather in Summerland Key into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. 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.