A calm river with boats, lush greenery, and a clear blue sky.

Find Hotels with a Pool in Big Pine Key, FL

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
  • Be picky

    Search almost a million properties worldwide

Check availability on Big Pine Key Hotels with a Pool

Tonight
Oct 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Big Pine Key hotels with a pool

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.
$166 nightly
$187 total
Oct 26 - Oct 27
Total with taxes and fees
Blue Flamingo Resort Key West

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.
$186 nightly
$210 total
Oct 26 - Oct 27
Total with taxes and fees
Southernmost Beach Resort and Guesthouses

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

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.
$255 nightly
$287 total
Oct 26 - Oct 27
Total with taxes and fees
Margaritaville Beach House Key West

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.
$219 nightly
$246 total
Nov 15 - Nov 16
Total with taxes and fees
Havana Cabana at Key West

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.
$306 nightly
$344 total
Nov 2 - Nov 3
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton

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.
$262 nightly
$295 total
Oct 26 - Oct 27
Total with taxes and fees
Isla Bella Beach Resort & Spa

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
$167 total
Oct 29 - Oct 30
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West

9. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
  • Splash into paradise at four tropical pools with poolside dining and coastal shuttles.
$194 nightly
$218 total
Oct 26 - Oct 27
Total with taxes and fees
Parrot Key Hotel & Villas

10. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
  • Poolside bliss awaits with cocktails, sun loungers, and a hot tub for ultimate relaxation.
$135 nightly
$152 total
Oct 29 - Oct 30
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
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

Find out more about Big Pine Key

Discover top Big Pine Key attractions

Big Pine Key offers a delightful blend of natural beauty and unique activities that will captivate any traveler. One must-visit spot is the vibrant nature trails of the local preserve, where you can immerse yourself in the stunning flora and fauna, perfect for those who appreciate the tranquility of the great outdoors. For a taste of adventure, exploring the nearby mangroves by kayak allows you to glide through serene waters while spotting native wildlife. Don’t miss the breathtaking sunsets at the beach, where the sky transforms into a canvas of colors—a perfect backdrop for family photos. For a touch of local culture, take a leisurely stroll through charming neighborhoods that showcase the area's distinct architecture and friendly atmosphere. Finally, the nearby fishing spots offer opportunities for family bonding, whether you’re casting a line or simply enjoying the scenic views. With such a variety of experiences, you’ll find that Big Pine Key is not just a destination, but a chance to create lasting memories. Consider staying in one of the charming accommodations nearby, where attentive service and comfortable settings will ensure your family feels pampered throughout your visit.

Top Big Pine Key Hotel Reviews

Kingsail Resort

Kingsail Resort

10/10 Excellent
"Great value for the price"
Nicholas 1-night trip
Posted less than an hour ago
Kingsail Resort
Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys

10/10 Excellent
"The hotel was extremely clean. The rooms were extremely clean. We had a suite which was absolutely excellent. The bar and restaurant on property site were extremely well maintained."
Ted 3-night trip
Posted 3 hours ago
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Parmer's Resort

Parmer's Resort

10/10 Excellent
"Nice property! Large clean room, swimming pool, laundry available, nice fresh grab and go breakfast. Outside area was on the water and nice, but didn’t have time to enjoy it. Wish they had an ironing board and iron in the room."
Jolee 1-night trip
Posted 15 hours ago
Parmer's Resort
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 6 days ago
Old Wooden Bridge Resort and 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 2 weeks 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.

Explore a world of travel with Expedia