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 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
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 hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
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 modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

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 beachside lounge with chairs and umbrellas, overlooking the ocean.
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.
$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 white building with a covered patio area, surrounded by palm trees and a view of the ocean.
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 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 person standing by a window overlooking a beach with palm trees and the ocean.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.
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 cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

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.
$226 nightly
$254 total
Oct 21 - Oct 22
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 beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.
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.
$215 nightly
$242 total
Oct 25 - Oct 26
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 with white chairs and kayaks, palm trees, and a clear view of the ocean.
Room
A bar area with wooden chairs, a bar counter, and a variety of bottles and glasses.

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.
$276 nightly
$310 total
Oct 21 - Oct 22
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 sofa, a small table, a lamp, and a balcony with chairs.
A hotel room with a large bed, a desk, a chair, a small table, and a balcony with a view of palm trees.

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 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.
$193 nightly
$217 total
Oct 28 - Oct 29
Total with taxes and fees
Beachside Resort & Residences
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.

10. 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
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

Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

10/10 Excellent
"Villa was clean. Staff was very polite, knowledgeable. There was a problem with the toilet and it was taken care of. A shower outside of the pool area would be very helpful in washing off sandy feet, also a door mat. Silverware was very cheap, could be better. It's the small things that could make it great."
Cynthia 2-night trip
Posted 4 hours ago
Tranquility Bay Beachfront Hotel and Resort
Kingsail Resort

Kingsail Resort

10/10 Excellent
"Buena ubicación, buen trato del personal, súper limpio. La unidad tiene cocina que es súper práctica. Lo único que no nos gustó fue que al estar hospedados en plata Baja escuchábamos todos los movimientos de los vecinos del piso superior"
Cristian 2-night trip
Posted 5 hours ago
Kingsail Resort
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 11 hours ago
Parmer's Resort
Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys

10/10 Excellent
"The lunchtime waitress in the bar/restaurant was incredibly lively & full of drive. She really made our day. Room good size, clean & adequate."
Rene 1-night trip
Posted 12 hours ago
Fairfield Inn & Suites by Marriott Marathon Florida Keys
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 13 hours ago
Old Wooden Bridge Resort and Marina
Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

10/10 Excellent
"The room was clean and smelled very good .The air was on when we came in ,so it was a good temperature as well .Staff was friendly and attentive ."
Gretchen 1-night trip
Posted 13 hours ago
Captain Pips Marina & Hideaway
Coconut Cay Resort & Marina

Coconut Cay Resort & Marina

10/10 Excellent
"muy recomendable muy buen servicio centrico"
yurizan 1-night trip
Posted 14 hours ago
Coconut Cay Resort & 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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