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 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A couple holding hands in a tropical setting with palm trees and greenery.

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 11 - Oct 12
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 balcony with white railings, a view of the beach, and palm trees.
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.
$211 nightly
$238 total
Oct 11 - Oct 12
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 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 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.
$198 nightly
$223 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 person standing by a window overlooking a beach with palm trees and the ocean.
A beach with a palm tree and two chairs.

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 8 - Oct 9
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.
Room
A bar area with wooden chairs, a bar counter, and a variety of bottles and glasses.
A beach scene with two white chairs, a hammock, and palm trees.

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.
$355 nightly
$399 total
Oct 8 - Oct 9
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 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.
$276 nightly
$310 total
Oct 25 - Oct 26
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 spacious lobby with a central seating area, two staircases, and multiple potted plants.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.
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.
$197 nightly
$222 total
Oct 25 - Oct 26
Total with taxes and fees
Havana Cabana at Key West
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
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.
A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

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 14 - Oct 15
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 beach view with a wooden pier, palm trees, and a sunset over the water.
A balcony with wicker furniture, a view of the water, and a railing.
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.
$192 nightly
$216 total
Oct 8 - Oct 9
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 hotel with multiple colorful buildings, a pool area, and a boat dock.
A marina with boats docked, a beach resort building, and palm trees.
A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

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.
$172 nightly
$193 total
Oct 8 - Oct 9
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

Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

10/10 Excellent
"My husband and I started coming here about a year and a half ago. We absolutely love it here. You are in the middle part of the keys so you can get to upper and lower keys and still have plenty of time to explore for the day. We have stayed at a couple other places however they do not compare to Captain Pips. It is very quiet there in the evenings with amazing views on the water. The maid Kira is so welcoming. Always has a smile on her face. Anything you need from towels to clean sheets she is happy to help! Staff is friendly, property is well maintained. I won’t stay anywhere else when going there. Prices are great too!!Great place to stay."
Sally 4-night trip
Posted 12 hours ago
Captain Pips Marina & Hideaway
Kingsail Resort

Kingsail Resort

10/10 Excellent
"Quite and Relaxing place."
IRAN G 1-night trip
Posted 22 hours ago
Kingsail Resort
Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys

10/10 Excellent
"Great hotel staff was friendly, breakfast was top notch and the pool sensational"
Ismael 1-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"This is a great inexpensive place to stay. Room was clean. Resort is showing some wear but is still good. Staff are very helpful with local recommendations. There is a great gas station next door with some items for sale in case you forget something. I would stay again."
Brandy 2-night trip
Posted 2 days ago
Looe Key Reef Resort
Parmer's Resort

Parmer's Resort

10/10 Excellent
"Just a fantastic property, wonderful staff, great amenities, so many waterfront places to chill. Immaculate grounds with a laid back vibe, loved it!!"
Moira 1-night trip
Posted 4 days ago
Parmer's Resort
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 13 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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