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

Check availability on Summerland Key Hotels with a Pool

Tonight
Sep 11 - Sep 12
Tomorrow
Sep 12 - Sep 13
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Summerland Key hotels with a pool

A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

1. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$82 nightly
$92 total
Oct 12 - Oct 13
Total with taxes and fees
Looe Key Reef Resort
A sunset view with a thatched structure and a palm tree by a calm body of water.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.
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.

2. 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.
$156 nightly
$175 total
Sep 27 - Sep 28
Total with taxes and fees
Parmer's Resort
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.
A waterfront building with a flat roof, large windows, and a balcony.
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.
$119 nightly
$134 total
Sep 13 - Sep 14
Total with taxes and fees
Sugar Loaf Lodge
A marina with boats, a dock, and a white building with a balcony.
A spacious living area with a wooden ceiling, a ceiling fan, a TV, a glass coffee table, a sofa, a chair, and a kitchen area with a refrigerator and bar stools.
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.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$366 nightly
$407 total
Sep 13 - Sep 14
Total with taxes and fees
SAVE BIG $$$ 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 waterfront property with a two-story building, a covered outdoor area, and a dock.
A marina with RVs docked along a waterway, surrounded by palm trees and buildings.
A balcony with a view of neighboring houses, a street, and a clear sky.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$366 nightly
$407 total
Sep 13 - Sep 14
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A swimming pool with blue and white tiled edges, surrounded by palm trees and white lounge chairs.
A white building with large windows and a balcony, featuring outdoor furniture and a covered area.
A balcony with white chairs and a table, overlooking a pool and a marina with boats.
A kitchen with white cabinets, a microwave, a stove, a sink, and a refrigerator.

6. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
Canal Front home with easy Ocean access
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.

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

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
$460 nightly
$511 total
Sep 12 - Sep 13
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.
A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.
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.

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
$526 nightly
$583 total
Sep 14 - Sep 15
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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
$497 nightly
$551 total
Sep 12 - Sep 13
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.

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
$514 nightly
$571 total
Sep 12 - Sep 13
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 spacious living area with a wooden ceiling, a ceiling fan, a TV, a glass coffee table, a sofa, a chair, and a kitchen area with a refrigerator and bar stools.
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.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$366 nightly
$407 total
Sep 13 - Sep 14
Total with taxes and fees
SAVE BIG $$$ 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
$460 nightly
$511 total
Sep 12 - Sep 13
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

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
$497 nightly
$551 total
Sep 12 - Sep 13
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.
A beachfront property with a large building, palm trees, and a sandy area.
An electrical box with warning labels and a view of a marina with boats and palm trees.
A coastal residential area with white houses, palm trees, and a clear blue sky.

Venture Out RV lot 223

Venture Out RV lot 223
Cudjoe key
$228 nightly
$241 total
Sep 12 - Sep 13
Total with taxes and fees
Venture Out RV lot 223
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.
A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.
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.

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$526 nightly
$583 total
Sep 14 - Sep 15
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A covered outdoor area with wicker furniture and string lights.

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
$514 nightly
$571 total
Sep 12 - Sep 13
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A beachfront property with a pool, palm trees, and a two-story building.
A marina with waterfront properties, including a docked boat and a small dock with a table and chairs.
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.

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
$256 nightly
$275 total
Sep 12 - Sep 13
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A resort with a swimming pool, beach area, and marina.
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
$545 nightly
$604 total
Sep 12 - Sep 13
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 resort with a swimming pool, beach area, and marina.
A marina with several white mobile homes, a swimming pool, and a trailer.

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
$556 nightly
$617 total
Sep 12 - Sep 13
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A resort with a swimming pool, beach area, and marina.
A covered outdoor area with a glass table and chairs, overlooking a body of water and a distant island.

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
$568 nightly
$630 total
Sep 12 - Sep 13
Total with taxes and fees
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
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

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Amazing"
Julie 2-night trip
Posted 4 days ago
Sugar Loaf Lodge
Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"Nice"
Lakpathi 1-night trip
Posted 5 days ago
Looe Key Reef Resort

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. 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 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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