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 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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 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.
$175 nightly
$197 total
Oct 12 - Oct 13
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.
$239 nightly
$269 total
Oct 26 - Oct 27
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 spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
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.

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 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.
A person standing by a window overlooking a beach with palm trees and 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 12 - Oct 13
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 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.

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.
$271 nightly
$305 total
Oct 18 - Oct 19
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 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.

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 covered outdoor seating area with a pool in the background.
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.

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.
$187 nightly
$210 total
Oct 14 - Oct 15
Total with taxes and fees
Havana Cabana at Key West
A balcony with a view of a pool area, palm trees, and outdoor seating.
A modern bathroom with a shower, a sink, and a mirror.
A large conference room with round tables, chairs, and a central carpeted area.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and 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.
$157 nightly
$177 total
Oct 27 - Oct 28
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 view of the sea, and a spiral staircase.

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 12 - Oct 13
Total with taxes and fees
Beachside Resort & Residences
A pool area with blue lounge chairs, a hot tub, and a covered seating area.
A marina with boats docked, a beach resort building, and palm trees.
A hotel room with a bed, a view of the beach, a hammock, and beach chairs.
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.
$175 nightly
$197 total
Oct 12 - Oct 13
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

Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"Great diving"
Gerald 3-night trip
Posted 17 hours ago
Looe Key Reef Resort
Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys

10/10 Excellent
"Dinette who is the Marina Manager is the top star associated with Fairfield Inn and Suites at Marathon. We visited her several times to gather information so we could enjoy our vacation as much as possible. She personally made phone calls to other vendors to confirm details on our behalf. She made recommendations for restaurants, coffee, and general shopping. She attempted to help us reserve a parasailing trip outside of Key West (more locally). The owner of Z’s Parasailing, located right at the property, was otherwise committed until after the end of our trip. Dinette helped him understand how much we had been valuing this activity. Captain Howard instead offered us a different water activity that turned out to be just as spectacular. He did this completely out of the goodness of his heart. Please pay his interest in ensuring the resort guests had a wonderful experience forward by giving him more business than he could dream of. Stay local, support this small business, support honestly good people. Dinette didn’t have to expend an ounce of energy toward us beyond communicating that the marina couldn’t help at that very specific time. Howard didn’t have to problem-solve an alternative solution to our parasailing request. Dinette didn’t have to engage the many other visitors to the store like I heard her doing so during our time. Fairfield Inn and Suites have two superb stewards of a customer service orientation. How fortunate for Fairfield, us, and for you."
Jill Ann 2-night trip
Posted 17 hours ago
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Kingsail Resort

Kingsail Resort

10/10 Excellent
"The staff was very accommodating. The coffee by the water was fantastic. We loved going kayaking at sunset! Very amazing place to stay!"
Caroline 3-night trip
Posted 21 hours ago
Kingsail Resort
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

10/10 Excellent
"Access to the beach for the kids"
Rene 4-night trip
Posted 1 day ago
Tranquility Bay Beachfront Hotel and Resort
Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

10/10 Excellent
"Anna, Katelyn and Penny at the front desk are ALWAYS helpful! This keeps us coming back! Beautiful facility on the Bayside. Big rooms, Great fishing, Great Kayaks in Lagoon.Great location! They are great on the little things too that matter. Greatest and Cheapest boat rentals !"
Joseph 1-night trip
Posted 2 days ago
Captain Pips Marina & Hideaway
Parmer's Resort

Parmer's Resort

10/10 Excellent
"Fishing charter guide pick up from dock every morning. G"
Dennis 3-night trip
Posted 3 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 2 weeks 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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