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 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
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 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 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.
A balcony with white railings, a view of the beach, and palm trees.

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.
$225 nightly
$253 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.
$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.
$260 nightly
$293 total
Oct 30 - Oct 31
Total with taxes and fees
Margaritaville Beach House Key West
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 bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen 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.
$201 nightly
$227 total
Nov 1 - Nov 2
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 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.

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.
$208 nightly
$234 total
Oct 19 - Oct 20
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.
Room
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.
$283 nightly
$318 total
Oct 18 - Oct 19
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 modern bathroom with a shower, a sink, and a mirror.
A hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.
A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.

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 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 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.
A balcony with wicker furniture, a view of the water, and a railing.

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 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.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

10. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$139 nightly
$157 total
Oct 28 - Oct 29
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

8/10 Good
"Good trip"
allen 1-night trip
Posted 5 hours ago
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Banana Bay Resort & Marina

Banana Bay Resort & Marina

8/10 Good
"The rooms are modern and clean. The hotel area is rustic as it should be in the keys. My only complaint is the fees. Parking fees and hotel/service fees... Oh, and the beautiful bar with the perfect water view is only open for two hours (during sunset)."
Amil 1-night trip
Posted 6 hours ago
Banana Bay Resort & Marina
Parmer's Resort

Parmer's Resort

10/10 Excellent
"I've stayed at Parmers several times and anytime I'm in the Keys Parmers is where I stay. Staff is excellent."
Ken 2-night trip
Posted 6 hours ago
Parmer's Resort
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

10/10 Excellent
"N/a"
Aidelyn 2-night trip
Posted 1 day ago
Tranquility Bay Beachfront Hotel and Resort
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

8/10 Good
"Staff was very pleasant. But the stay was not cheap. And I have two "issues". First - We had a breakfast plan with the room and we were given 2 $25 vouchers (1 each) for the two days we stayed. When I viewed the initial bill, we were billed $50 for breakfast on the first day, even though we used the vouchers. The hotel staff removed that charge when I brought it up to them, but it shouldn't have been there in the first place. Second issue - We arrived around 2 pm on Sunday and left around Noon on Tuesday. Parking was $20 per day. When I viewed the final bill, we were charged for 3 days of parking, even though we spent less than 48 hours at the hotel. Yes, the car was in the lot one full day and part of 2 other days, but I have NEVER been charged for 3 days parking at ANY HOTEL EVER when I spent just two nights in the hotel. Generally, parking follows the room charge - 2 days room = 2 days parking. I think that is really poor given that this is an expensive resort managed by a major hotel chain."
Philip 2-night trip
Posted 1 day ago
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

10/10 Excellent
"Really good place the room we had was the flounder and it was super fantastic"
Todd c 2-night trip
Posted 2 days ago
Captain Pips Marina & Hideaway
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

10/10 Excellent
"As soon as we"
Stephen 4-night trip
Posted 2 days ago
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton
Coconut Cay Resort & Marina

Coconut Cay Resort & Marina

10/10 Excellent
"Great location, amazing prize!! Conveniently Located in the heart of Marathon, easy access to many great spots and restaurants."
Chet 3-night trip
Posted 4 days ago
Coconut Cay Resort & Marina
Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"They had a nice pool you could park your boat in the channel they also had a very nice tiki bar and grill it was an ok place to stay but parking sucked"
Todd c 1-night trip
Posted 4 days ago
Looe Key Reef Resort

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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