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

Find Hotels with a Pool in Big Pine Key, FL

Check availability on Big Pine Key Hotels with a Pool

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
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 spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A couple holding hands in a tropical setting with palm trees and greenery.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

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.
$166 nightly
$187 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 balcony with white railings, a view of the beach, and palm trees.
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.

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.
$235 nightly
$265 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.
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.

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.
$178 nightly
$200 total
Nov 1 - Nov 2
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 hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.
A beach with a palm tree and two chairs.
A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.

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.
$275 nightly
$310 total
Oct 25 - Oct 26
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 covered outdoor seating area with a pool in the background.
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.
$236 nightly
$265 total
Oct 30 - Oct 31
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 wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A spacious lobby with green sofas, a coffee table, and a dining area.
A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

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.
$289 nightly
$325 total
Oct 29 - Oct 30
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.
A beach scene with two white chairs, a hammock, and palm trees.
A bar area with wooden chairs, a bar counter, and a variety of bottles and glasses.
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.
$294 nightly
$331 total
Oct 26 - Oct 27
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 room with a sofa, a small table, a lamp, and a balcony with chairs.
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.
A modern hotel room with a balcony, a grey sofa, a red chair, a white coffee table, and a painting of a tropical scene.

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.
$137 nightly
$154 total
Oct 29 - Oct 30
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 water, and a railing.
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.

9. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
$202 nightly
$227 total
Oct 25 - Oct 26
Total with taxes and fees
Beachside Resort & Residences
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
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.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

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

Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys

10/10 Excellent
"Just wow! Everything was amazing."
Priyanka 2-night trip
Posted 5 hours ago
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Parmer's Resort

Parmer's Resort

10/10 Excellent
"All Aspects"
William 7-night trip
Posted 8 hours ago
Parmer's Resort
Coconut Cay Resort & Marina

Coconut Cay Resort & Marina

10/10 Excellent
"We stayed here for one night during our visit to Marathon in the Florida Keys. The location was nice enough and convenient for exploring the area. Our room was situated at the front of the property, so there was quite a lot of road and car park noise, although this was somewhat expected given the location. It did feel as though the front window was open, despite being closed, as it did very little to block out the outside noise. On the positive side, the room was incredibly spacious, with a lovely large TV and a super comfortable bed. The shower was great, and the amenities provided were good. Ice and drinks were also available from reception, which was handy. The reception staff were exceptionally friendly and welcoming. The air conditioning worked overtime but didn’t seem to cool the room particularly well and was rather noisy itself. However, this was more of a minor observation than a complaint. The only real disappointment was the cleanliness of the floor. After showering, the floor became slightly wet, and walking around barefoot left the bottoms of my feet noticeably dirty, which was a shame. Overall, a perfectly reasonable place to stay for a night in Marathon. A few minor improvements would make a difference, but we had a comfortable stay, and the friendly staff were certainly a highlight."
Shirley 1-night trip
Posted 23 hours ago
Coconut Cay Resort & Marina
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

10/10 Excellent
"Beautiful infinity pool. Very helpful front desk staff at check in and check out. Thank you for a great stay!"
Kathleen 3-night trip
Posted 1 day ago
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

10/10 Excellent
"Nice layout"
Michael 3-night trip
Posted 1 day ago
Tranquility Bay Beachfront Hotel and Resort
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

8/10 Good
"I enjoyed my stay in the Aqualodge, it was peaceful and relaxed. The view was great and I enjoyed watching the sunrise daily."
Anonymous traveler 3-night trip
Posted 2 days ago
Old Wooden Bridge Resort and Marina

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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