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
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

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.
$148 nightly
$167 total
Aug 25 - Aug 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 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.

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$100 nightly
$112 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 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.
A waterfront building with a flat roof, large windows, and a balcony.

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
Aug 25 - Aug 26
Total with taxes and fees
Sugar Loaf Lodge
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.

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

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$450 nightly
$499 total
Aug 29 - Aug 30
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a swimming pool, beach area, and marina.
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
$460 nightly
$511 total
Sep 4 - Sep 5
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 living room with a television displaying a show, a ceiling fan, and a window with blinds.
A bathroom with a toilet, sink, and bathtub.

6. 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
$580 total
Aug 25 - Aug 26
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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
$512 nightly
$568 total
Aug 25 - Aug 26
Total with taxes and fees
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 marina with waterfront properties, including a docked boat and a small dock with a table and chairs.
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.

8. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
$257 nightly
$276 total
Aug 25 - Aug 26
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
A resort with a swimming pool, beach area, and marina.
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.

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

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
$549 nightly
$608 total
Aug 25 - Aug 26
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.
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.
A marina with RVs docked along a waterway, surrounded by palm trees and buildings.

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

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$473 nightly
$525 total
Aug 26 - Aug 27
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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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 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 $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$450 nightly
$499 total
Aug 29 - Aug 30
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. 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 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
$460 nightly
$511 total
Sep 4 - Sep 5
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
$512 nightly
$568 total
Aug 25 - Aug 26
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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 living room with a television displaying a show, a ceiling fan, and a window with blinds.
A clear view of a lobster underwater, surrounded by a rocky seabed.

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
$580 total
Aug 25 - Aug 26
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
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
$514 nightly
$571 total
Sep 1 - Sep 2
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 living room with a sofa, armchair, TV, and a view of the outdoors.

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
$560 nightly
$621 total
Aug 25 - Aug 26
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
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 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
Aug 31 - Sep 1
Total with taxes and fees
Venture Out RV lot 223
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 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
Aug 25 - Aug 26
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 covered outdoor area with a glass table and chairs, overlooking a body of water and a distant island.
A resort with a swimming pool, beach area, and marina.

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

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
$573 nightly
$635 total
Sep 6 - Sep 7
Total with taxes and fees
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
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
$560 nightly
$621 total
Aug 25 - Aug 26
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.
View all properties

Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Me gustaría más opciones como un regular desayuno"
Susana 2-night trip
Posted 7 hours ago
Sugar Loaf Lodge
Parmer's Resort

Parmer's Resort

8/10 Good
"We stayed at Parmer’s Resort for just one night and overall had a great experience. The room was clean and comfortable, and the staff was very helpful and friendly. They gave us excellent recommendations for places to visit in the area. Based on their recommendation, we decided to visit Kiki’s Sandbar, and we absolutely loved it! The food was delicious, the drinks were great, and the live music and atmosphere made it a really enjoyable experience. Everything about our stay was excellent, and we appreciated how helpful the staff was. I decided to give 4 stars instead of 5 only because we did not have hot water in the shower. Other than that, we had a wonderful stay and would definitely recommend Parmer’s Resort!"
Raulise 1-night trip
Posted 10 hours ago
Parmer's Resort
Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"Great clean place to stay with a great tiki bar/restaurant/pool and fabulous dive/snorkle center on site with a fabulous crew that takes you to the protected Looe Key Reef. Highly recommend the water trip over anything in Key West,"
Bonita 4-night trip
Posted 8 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. 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 Venture 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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