A calm river with boats, lush greenery, and a clear blue sky.

Find Hotels with a Pool in Big Pine Key, FL

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Check availability on Big Pine Key Hotels with a Pool

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Big Pine Key hotels with a pool

A clear blue pool surrounded by lounge chairs and umbrellas, with palm trees and a gazebo in the background.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
A couple holding hands in a tropical setting with palm trees and greenery.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

1. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
  • Float in paradise at two scenic pools with cabanas, surrounded by stunning sunset views and tropical relaxation.
$175 nightly
$197 total
Oct 25 - Oct 26
Total with taxes and fees
Blue Flamingo Resort Key West
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.
A beachfront hotel with multiple-story buildings, palm trees, and a sandy beach.
A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.
A balcony with white railings, a view of the beach, and palm trees.

2. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
  • Dive into a serene escape at this beachfront resort with 3 outdoor pools, poolside bars, and tranquil ocean views.
$239 nightly
$269 total
Oct 25 - Oct 26
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
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 white building with a covered patio area, surrounded by palm trees and a view of the ocean.

3. 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.
$184 nightly
$207 total
Nov 18 - Nov 19
Total with taxes and fees
Parmer's Resort
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A person standing by a window overlooking a beach with palm trees and the ocean.
A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

4. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
  • Float in serene waters at this sun-soaked poolside paradise with direct beach access and friendly round-the-clock service.
$265 nightly
$298 total
Oct 19 - Oct 20
Total with taxes and fees
Margaritaville Beach House Key West
A swimming pool surrounded by palm trees and a natural rock formation.
A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.
A spacious lobby with a central seating area, two staircases, and multiple potted plants.

5. Havana Cabana at Key West

Havana Cabana at Key West
New Town
  • Poolside paradise awaits with hot tub, dining, and bar service at this vibrant Key West oasis.
$200 nightly
$225 total
Nov 3 - Nov 4
Total with taxes and fees
Havana Cabana at Key West
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.
A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.
A spacious lobby with green sofas, a coffee table, and a dining area.
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

6. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
  • Crystal blue waters beckon from private beach paradise with 2 outdoor pools and a luxurious beachside bar.
$276 nightly
$310 total
Nov 1 - Nov 2
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
An aerial view of a resort with a central pool, multiple buildings, and a beach area with sun loungers.
Room
A beach scene with two white chairs, a hammock, and palm trees.
A beach with white chairs and kayaks, palm trees, and a clear view of the ocean.

7. Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa
Marathon
  • Sun-kissed island retreat offers five heated pools with loungers and poolside cocktails.
$252 nightly
$283 total
Oct 20 - Oct 21
Total with taxes and fees
Isla Bella Beach Resort & Spa
A balcony with a view of a pool area, palm trees, and outdoor seating.
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.
A hotel room with a large bed, a desk, a chair, a small table, and a balcony with a view of palm trees.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.

8. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
  • Splash into tropical paradise at this resort's cabana-lined pool with views and poolside cocktails.
$149 nightly
$168 total
Oct 25 - Oct 26
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.
A balcony with wicker furniture, a view of the sea, and a spiral staircase.
A beach view with a wooden pier, palm trees, and a sunset over the water.
A balcony with wicker furniture, a red chair, and a lamp.

9. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
$201 nightly
$226 total
Oct 26 - Oct 27
Total with taxes and fees
Beachside Resort & Residences
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 rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

10. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$140 nightly
$158 total
Oct 26 - Oct 27
Total with taxes and fees
Looe Key Reef Resort
View all properties

Choose what matters most at hotels with a pool in Big Pine Key

Breakfast included
Hot tub
4 stars
Beach
5 stars

Top Big Pine Key Hotel Reviews

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

10/10 Excellent
"Loved it"
Siddharth 3-night trip
Posted 3 hours ago
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

8/10 Good
"It is very clean. Extremely easy check in & check out. Friendly staff. Nice view & pool. Access to kayak rentals. Good animal watching. Big bridge to fish off of nearby."
STEPHANIE 1-night trip
Posted 1 day ago
Old Wooden Bridge Resort and Marina
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

10/10 Excellent
"All around great hotel. Private pools for adults to enjoy peacefully, a big family pool, a nice beach, excellent Cuban breakfast across the street, and the staff were uniformly helpful and friendly."
Brett 4-night trip
Posted 2 days ago
Tranquility Bay Beachfront Hotel and Resort
Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

10/10 Excellent
"Great place to stay. Right on the water, very clean, and a nice location. Check in/check out process was easy. Would highly recommend and will be coming back."
Kaeli 4-night trip
Posted 2 days ago
Captain Pips Marina & Hideaway
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 3 days ago
Parmer's Resort
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

10/10 Excellent
"As soon as we"
Stephen 4-night trip
Posted 5 days ago
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Frequently asked questions

What are some accommodations with pools in Big Pine Key?
Old Wooden Bridge Resort and Marina: Features free self parking, an outdoor pool, and complimentary wireless internet access. Sunshine Key RV Resort & Marina: Offers a private beach, an outdoor pool, and sun loungers. Charming 3-bedroom house in Big Pine Key near Beach and Key West: Hotel located near Sombrero Beach. Features a full-service spa, 5 outdoor pools, and 2 bars. Isla Bella Beach Resort & Spa: Offers a snack bar/deli, 2 outdoor pools, and buffet. Fairfield Inn & Suites by Marriott Marathon Florida Keys: Features a private beach, an outdoor pool, and daily.
What is there to see and do in Big Pine Key?
Explore places like Florida Keys Beaches while you're in Big Pine Key. Spend some time experiencing the great outdoors at Calusa Beach and Cook Island.
When is the best time to book a hotel with a pool in Big Pine Key?
Taking into account the local weather in Big Pine Key can help you maximize your time at the pool during your trip. 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 72°F. Average annual precipitation for Big Pine Key is 36 inches.

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