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 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 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.
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.
$168 nightly
$189 total
Oct 4 - Oct 5
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 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 beachfront hotel with multiple-story buildings, palm trees, and a sandy beach.
A beachside lounge with chairs and umbrellas, overlooking the ocean.

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.
$261 nightly
$294 total
Oct 8 - Oct 9
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.
$156 nightly
$175 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 beach with a palm tree and two chairs.
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.

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 4 - Oct 5
Total with taxes and fees
Margaritaville Beach House Key West
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.
A bar area with wooden chairs, a bar counter, and a variety of bottles and glasses.
Room

5. Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa
Marathon
  • Sun-kissed island retreat offers five heated pools with loungers and poolside cocktails.
$256 nightly
$288 total
Oct 4 - Oct 5
Total with taxes and fees
Isla Bella Beach Resort & Spa
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 beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.
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.
$309 nightly
$348 total
Oct 4 - Oct 5
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
A swimming pool surrounded by palm trees and a natural rock formation.
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.
A covered outdoor seating area with a pool in the background.

7. 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.
$182 nightly
$205 total
Nov 1 - Nov 2
Total with taxes and fees
Havana Cabana at Key West
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
A hotel with a central courtyard, palm trees, and a fountain.
An outdoor patio with tables and chairs, umbrellas, and palm trees.
A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.

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 8 - Oct 9
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 balcony with wicker furniture, a red chair, and a lamp.
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.
$185 nightly
$208 total
Oct 4 - Oct 5
Total with taxes and fees
Beachside Resort & Residences
A pool area with blue lounge chairs, a hot tub, and a covered seating area.
A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.
A marina with boats docked, a beach resort building, and palm trees.
A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

10. Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
  • Splash into paradise at this Art Deco hotel with a poolside bar and marina access.
$184 nightly
$207 total
Oct 4 - Oct 5
Total with taxes and fees
Ibis Bay Beach 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
"Great propert"
Scott 5-night trip
Posted 4 hours ago
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Kingsail Resort

Kingsail Resort

10/10 Excellent
"My Dad and myself had an Awesome stay everything was clean well kept beautifully piece of property with a nice Clean pool, Rcommend anybody would like to stay at this Place!!!🏝️🐬😊"
Carl 3-night trip
Posted 13 hours ago
Kingsail Resort
Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

8/10 Good
"Room was clean and nice. Didn’t have alot of room in the bathroom, small sink no where to put things even in the shower. But overall great stay."
Jessica 3-night trip
Posted 15 hours ago
Captain Pips Marina & Hideaway
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

10/10 Excellent
"Great"
Kevin 4-night trip
Posted 16 hours ago
Tranquility Bay Beachfront Hotel and Resort
Banana Bay Resort & Marina

Banana Bay Resort & Marina

10/10 Excellent
"Staff was nice and room clean"
Alexis 3-night trip
Posted 1 day ago
Banana Bay Resort & Marina
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

10/10 Excellent
"Everything is wonderful"
Arelis 2-night trip
Posted 3 days ago
Sunshine Key RV Resort & Marina
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

10/10 Excellent
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
Daisybel 2-night trip
Posted 6 days ago
Old Wooden Bridge Resort and Marina
Skipjack Resort & Marina

Skipjack Resort & Marina

10/10 Excellent
"Great spot"
Justin 2-night trip
Posted 2 months ago
Skipjack 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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