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 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 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.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

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.
$178 nightly
$200 total
Nov 1 - Nov 2
Total with taxes and fees
Parmer's 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 beachside dining area with thatched umbrellas, white plastic chairs, and tables.

2. 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 26 - Oct 27
Total with taxes and fees
Sugar Loaf Lodge
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
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.
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

3. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$142 nightly
$160 total
Oct 26 - Oct 27
Total with taxes and fees
Looe Key Reef Resort
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 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.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$388 nightly
$431 total
Oct 21 - Oct 22
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. OCEANFRONT 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.
Outdoor dining

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
$372 nightly
$413 total
Oct 27 - Oct 28
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Pool
Outdoor dining
Beach
Sport court

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
$410 nightly
$455 total
Nov 2 - Nov 3
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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 kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$403 nightly
$447 total
Oct 22 - Oct 23
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
Beach
A covered outdoor area with wicker furniture and string lights.
Sport court

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
$427 nightly
$475 total
Oct 21 - Oct 22
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 RVs and mobile homes, a swimming pool, and a view of the ocean.
Outdoor dining
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

9. 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
$439 nightly
$487 total
Oct 21 - Oct 22
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
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.

10. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
$243 nightly
$261 total
Oct 21 - Oct 22
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
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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 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.
Outdoor dining

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
$372 nightly
$413 total
Oct 27 - Oct 28
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
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 kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.
A marina with boats, a dock, and a white building with a balcony.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$403 nightly
$447 total
Oct 22 - Oct 23
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
Outdoor dining
Beach
Sport court

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
$410 nightly
$455 total
Nov 2 - Nov 3
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 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
$243 nightly
$261 total
Oct 21 - Oct 22
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
Pool
Beach
A covered outdoor area with wicker furniture and string lights.
Sport court

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 21 - Oct 22
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 RVs and mobile homes, a swimming pool, and a view of the ocean.
Outdoor dining
A resort with a swimming pool, beach area, and marina.

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
$439 nightly
$487 total
Oct 21 - Oct 22
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
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 beachside area with palm trees, picnic tables, and a view of the sea.
A resort with a swimming pool, beach area, and marina.

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

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
$498 nightly
$553 total
Oct 21 - Oct 22
Total with taxes and fees
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A playground with various play structures, including a climbing frame and a swing set, surrounded by a fence and palm trees.
A beachside pool area with lounge chairs, a thatched umbrella, and palm trees.
A swimming pool with palm trees and a view of the sea.
A gravel area with a manhole cover, a palm tree, and a building with a balcony.

Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West

Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West
Cudjoe Key
$133 nightly
$147 total
Oct 21 - Oct 22
Total with taxes and fees
Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West
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.
Living area
Marina

Canal-Front Retreat with Dock, Pool & Open Ocean Views

Canal-Front Retreat with Dock, Pool & Open Ocean Views
Cudjoe Key
$460 nightly
$510 total
Oct 22 - Oct 23
Total with taxes and fees
Canal-Front Retreat with Dock, Pool & Open Ocean Views
Pool
Outdoor dining
A living room with a sofa, armchair, TV, and a view of the outdoors.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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 21 - Oct 22
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Stay was perfect. Staff was kind and outgoing. Bed was comfortable and place was very clean. Only thing I would change is the single serve coffee makers. A drip pot would be so much more convenient. They do have Babies coffee in the dining hall at breakfast and I can not complain about that. I love Babies coffee. I will stay here again."
Denis 3-night trip
Posted 7 hours ago
Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
Mariia 1-night trip
Posted 1 day ago
Sugar Loaf Lodge
Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"They had a nice pool you could park your boat in the channel they also had a very nice tiki bar and grill it was an ok place to stay but parking sucked"
Todd c 1-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 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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