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 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

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 spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
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.
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.
$147 nightly
$166 total
Sep 25 - Sep 26
Total with taxes and fees
Parmer's Resort
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.
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.
$95 nightly
$107 total
Sep 23 - Sep 24
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 corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.

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 covered balcony with a table and chairs, a grill, and a boat docked nearby.
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 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 $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$366 nightly
$407 total
Sep 13 - Sep 14
Total with taxes and fees
SAVE BIG $$$ 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 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 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 $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$366 nightly
$407 total
Sep 15 - Sep 16
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a swimming pool, beach area, and marina.
A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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
$457 nightly
$508 total
Oct 1 - Oct 2
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

7. 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
$494 nightly
$548 total
Sep 13 - Sep 14
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.

8. 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
$511 nightly
$568 total
Sep 13 - Sep 14
Total with taxes and fees
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 marina with several white mobile homes, a swimming pool, and a trailer.
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.

9. 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
$553 nightly
$614 total
Sep 14 - Sep 15
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A resort with a swimming pool, beach area, and marina.
A marina with boats docked, a clear sky, and a calm waterway.
A coastal residential area with houses, a marina, and a flag.

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

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
$541 nightly
$600 total
Sep 13 - Sep 14
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
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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 bedroom with a bed, a ceiling fan, a window with blinds, and a door with a sign.
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 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 $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$366 nightly
$407 total
Sep 13 - Sep 14
Total with taxes and fees
SAVE BIG $$$ 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 room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.
A resort with a swimming pool, beach area, and marina.

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
$457 nightly
$508 total
Oct 1 - Oct 2
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
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
$494 nightly
$548 total
Sep 13 - Sep 14
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.
A large, two-story house with a balcony, a patio area with chairs, and a view of the water.
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
$220 nightly
$233 total
Sep 13 - Sep 14
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 compact kitchen with white cabinets, a refrigerator, a stove, and a dining area with a table and chairs.
A clear view of a lobster underwater, surrounded by a rocky seabed.
A living room with a television displaying a show, a ceiling fan, and a window with blinds.

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$522 nightly
$579 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
$511 nightly
$568 total
Sep 13 - Sep 14
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 residential street with houses, a driveway, and a gravel path.
A waterfront view with a marina, a boat docked, and a building with a balcony.
A marina with waterfront properties, including a docked boat and a small dock with a table and chairs.

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
$251 nightly
$270 total
Sep 13 - Sep 14
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 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
$541 nightly
$600 total
Sep 13 - Sep 14
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 resort with a swimming pool, beach area, and marina.
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
$553 nightly
$614 total
Sep 14 - Sep 15
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
$564 nightly
$626 total
Sep 13 - Sep 14
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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
Mireya 1-night trip
Posted 13 hours ago
Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Amazing"
Julie 2-night trip
Posted 5 days ago
Sugar Loaf Lodge
Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"Nice"
Lakpathi 1-night trip
Posted 6 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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