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 from CA $189

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Check availability on Summerland Key Hotels with a Pool

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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.
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.

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.
CA $208
CA $280 total
includes taxes & fees
Nov 3 - Nov 4
Parmer's Resort
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
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.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.

2. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
CA $168
CA $189 total
includes taxes & fees
Oct 27 - Oct 28
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 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.

3. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
CA $198
CA $223 total
includes taxes & fees
Nov 17 - Nov 18
Looe Key Reef Resort
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.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
CA $211
CA $619 total
includes taxes & fees
Oct 21 - Oct 22
SAVE BIG $$$ 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 coastal residential area with houses, a marina, and a flag.
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
CA $177
CA $591 total
includes taxes & fees
Oct 30 - Oct 31
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
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.
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.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
CA $226
CA $638 total
includes taxes & fees
Oct 19 - Oct 20
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
Beach
Outdoor dining
Sport court

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
CA $223
CA $650 total
includes taxes & fees
Nov 16 - Nov 17
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Pool
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.
Sport court
Beach

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
CA $245
CA $678 total
includes taxes & fees
Nov 14 - Nov 15
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 beachside area with palm trees, picnic tables, and a view of the sea.
A coastal residential area with houses, RVs, and a clear view of the ocean.

9. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
CA $319
CA $773 total
includes taxes & fees
Oct 18 - Oct 19
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Pool
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 living room with a sofa, armchair, TV, and a view of the outdoors.

10. 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
CA $297
CA $744 total
includes taxes & fees
Oct 18 - Oct 19
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
View all properties

Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"I've stayed at Parmers several times and anytime I'm in the Keys Parmers is where I stay. Staff is excellent."
Ken 2-night trip
Posted 1 day ago
Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

8/10 Good
"Balcony"
Martin 1-night trip
Posted 3 days 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 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 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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