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
Oct 9 - Oct 10
Tomorrow
Oct 10 - Oct 11
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Summerland Key hotels with a pool

A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.
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.

1. 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
Oct 11 - Oct 12
Total with taxes and fees
Sugar Loaf Lodge
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 spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

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.
$198 nightly
$223 total
Nov 1 - Nov 2
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 sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

3. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$101 nightly
$114 total
Oct 14 - Oct 15
Total with taxes and fees
Looe Key Reef Resort
A resort with a swimming pool, beach area, and marina.
Outdoor dining
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.

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

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
$375 nightly
$416 total
Oct 11 - Oct 12
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
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.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$388 nightly
$431 total
Oct 12 - Oct 13
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
Outdoor dining
Beach
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

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 nightly
$457 total
Oct 11 - Oct 12
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A resort with a swimming pool, beach area, and marina.
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.
A coastal residential area with houses, RVs, and a clear view of the ocean.

7. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
$489 nightly
$543 total
Oct 11 - Oct 12
Total with taxes and fees
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
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 waterfront property with a covered porch, a boat dock, and a clear sky.
A spacious living area with a ceiling fan, a television, and a seating area with a sofa and chairs.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$399 nightly
$443 total
Oct 13 - Oct 14
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
Beach
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.

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
$427 nightly
$475 total
Oct 14 - Oct 15
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 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.
Outdoor dining

10. 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
$442 nightly
$490 total
Oct 11 - Oct 12
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
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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 marina with boats, a dock, and a white building with a balcony.
A spacious living area with a ceiling fan, a television, and a seating area with a sofa and chairs.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$399 nightly
$443 total
Oct 13 - Oct 14
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
A living room with a sofa, armchair, TV, and a view of the outdoors.
A coastal residential area with houses, a marina, and a flag.
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
$468 nightly
$520 total
Oct 14 - Oct 15
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A spacious living room with a ceiling fan, a dining area with chairs, a kitchen with appliances, and a large window overlooking a balcony.
A living room with a sofa, a round table, a ceiling fan, a TV, and a view of the ocean through large windows.
A coastal residential area with houses, a marina, and a flag.

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
$486 nightly
$540 total
Oct 26 - Oct 27
Total with taxes and fees
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
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 living room with a television displaying a show, a ceiling fan, and a window with blinds.
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
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
Outdoor dining
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
$474 nightly
$526 total
Oct 12 - Oct 13
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Pool
Outdoor dining
Beach
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
$412 nightly
$457 total
Oct 11 - Oct 12
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
Outdoor dining
A coastal residential area with houses, a marina, and a flag.
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
$375 nightly
$416 total
Oct 11 - Oct 12
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Pool
Beach
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
$427 nightly
$475 total
Oct 14 - Oct 15
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.
Outdoor dining
A marina with boats docked, a clear sky, and a calm waterway.
A resort with a swimming pool, beach area, and marina.

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

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
$457 nightly
$507 total
Oct 13 - Oct 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 resort with a swimming pool, beach area, and marina.
Marina
Living area

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

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
$484 nightly
$537 total
Oct 11 - Oct 12
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
"Fishing charter guide pick up from dock every morning. G"
Dennis 3-night trip
Posted 1 day ago
Parmer's Resort
Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"This is a great inexpensive place to stay. Room was clean. Resort is showing some wear but is still good. Staff are very helpful with local recommendations. There is a great gas station next door with some items for sale in case you forget something. I would stay again."
Brandy 2-night trip
Posted 4 days ago
Looe Key Reef Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"
Richard 2-night trip
Posted 2 weeks 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 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 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 Out Keys.
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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