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

Find Hotels with a Pool in Summerland Key, FL

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Check availability on Summerland Key Hotels with a Pool

Tonight
Sep 2 - Sep 3
Tomorrow
Sep 3 - Sep 4
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

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.
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.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

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.
$195 nightly
$219 total
Sep 10 - Sep 11
Total with taxes and fees
Parmer's Resort
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 spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$75 nightly
$84 total
Sep 7 - Sep 8
Total with taxes and fees
Looe Key Reef Resort
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
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 corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

3. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
$101 nightly
$114 total
Sep 3 - Sep 4
Total with taxes and fees
Sugar Loaf Lodge
A marina with boats, a dock, and a white building with a balcony.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.
A covered balcony with a table and chairs, a grill, and a boat docked nearby.
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$367 nightly
$408 total
Sep 3 - Sep 4
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.
A balcony with a view of neighboring houses, a street, and a clear sky.
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.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$390 nightly
$433 total
Sep 3 - Sep 4
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. 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 room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.

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

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
$463 nightly
$514 total
Sep 4 - Sep 5
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A swimming pool with blue and white tiled edges, surrounded by palm trees and white lounge chairs.
A stone sculpture with a face, surrounded by rocks and palm trees.
A white building with large windows and a balcony, featuring outdoor furniture and a covered area.
A kitchen with white cabinets, a microwave, a stove, a sink, and a refrigerator.

7. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
$343 nightly
$381 total
Sep 9 - Sep 10
Total with taxes and fees
Canal Front home with easy Ocean access
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.
A bathroom with a toilet, sink, and bathtub.
A compact kitchen with white cabinets, a refrigerator, a stove, and a dining area with a table and chairs.
A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.

8. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$523 nightly
$581 total
Sep 8 - Sep 9
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

9. 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
$500 nightly
$554 total
Sep 3 - Sep 4
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A covered outdoor area with wicker furniture and string lights.
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.

10. 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
$513 nightly
$570 total
Sep 3 - Sep 4
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
Hot tub
4 stars
5 stars
Spa

Hotels with pools and hot tubs in Summerland Key

A waterfront property with a covered porch, a boat dock, and a clear sky.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.
A bedroom with a bed, a ceiling fan, a window with blinds, and a door with a sign.
A marina with boats, a dock, and a white building with a balcony.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$367 nightly
$408 total
Sep 3 - Sep 4
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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 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
$463 nightly
$514 total
Sep 4 - Sep 5
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A white building with large windows and a balcony, featuring outdoor furniture and a covered area.
A wooden bench on a gravel path by a calm body of water.
A kitchen with white cabinets, a microwave, a stove, a sink, and a refrigerator.
A stone sculpture with a face, surrounded by rocks and palm trees.

Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
$343 nightly
$381 total
Sep 9 - Sep 10
Total with taxes and fees
Canal Front home with easy Ocean access
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.
A clear view of a lobster underwater, surrounded by a rocky seabed.
A compact kitchen with white cabinets, a refrigerator, a stove, and a dining area with a table and chairs.
A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$523 nightly
$581 total
Sep 8 - Sep 9
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

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
$500 nightly
$554 total
Sep 3 - Sep 4
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A waterfront property with a concrete dock extending into calm water, a white building with a covered porch, and a palm tree.
An electrical box with warning labels and a view of a marina with boats and palm trees.
A beachfront property with a large building, palm trees, and a sandy area.
A large, two-story house with a balcony, a patio area with chairs, and a view of the water.

Venture Out RV lot 223

Venture Out RV lot 223
Cudjoe key
$229 nightly
$242 total
Sep 3 - Sep 4
Total with taxes and fees
Venture Out RV lot 223
A beachfront property with a pool, palm trees, and a two-story building.
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.
A waterfront view with a marina, a boat docked, and a building with a balcony.

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
$257 nightly
$276 total
Sep 3 - Sep 4
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
A covered outdoor area with wicker furniture and string lights.
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.

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
$513 nightly
$570 total
Sep 3 - Sep 4
Total with taxes and fees
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.
A marina with boats docked, a clear sky, and a calm waterway.
A coastal residential area with houses, a marina, and a flag.

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
$544 nightly
$603 total
Sep 3 - Sep 4
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A marina with several white mobile homes, a swimming pool, and a trailer.
A coastal residential area with houses, a marina, and a flag.

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
$555 nightly
$616 total
Sep 3 - Sep 4
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
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

Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"Everything was great! Staff was very friendly! Easy check in and check out."
christine 4-night trip
Posted 6 days ago
Looe Key Reef Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Me gustaría más opciones como un regular desayuno"
Susana 2-night trip
Posted 9 days ago
Sugar Loaf Lodge

Frequently asked questions

What's it like visiting Summerland Key?
If lounging next to a pool is your idea of a great vacation, you may want to consider Summerland Key, which has 27 places to stay with pools. During your visit, you can explore attractions like Florida Keys Beaches, and then kick back and relax poolside at one of the accommodations in Summerland Key that travelers like for their pools.
What are some accommodations 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 full-service spa. Sugarloaf Key RV Resort & Cottages: Provides a private beach, an outdoor pool, and a snack bar/deli. Sugar Loaf Lodge: Features free self parking, an outdoor pool, and complimentary wireless internet access. Looe Key Reef Resort: Hotel located near Florida Keys Beaches. Offers 2 outdoor tennis courts, an outdoor pool, and free self parking.
How many hotels with pools will I be able 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 like Florida Keys Beaches while you're in Summerland Key. Spend some time experiencing the great outdoors at Upper Sugarloaf Key and Pye Key.
When is the best time to book a hotel with a pool in Summerland Key?
Taking into account the local weather in Summerland Key is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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. Average annual precipitation for Summerland Key is 35 inches.

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