Find hotels with pools in Port Pine Heights, Big Pine Key from $111

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Check availability on Port Pine Heights Hotels with a Pool

Top Port Pine Heights Hotels with a Pool

Captain Pips Marina & Hideaway

3.0 star property
Marathon
  • Outdoor pool
  • Pool loungers
  • Near the beach
9.0 out of 10, Wonderful, (1015)
Swimming enthusiasts rejoice at the sun-drenched pool surrounded by comfortable loungers, perfect for relaxation after kayaking, snorkeling, or fishing excursions. This hotel combines maritime charm with convenient amenities including free bicycle rentals and a seafood restaurant.
$98 nightly
The price is $111
Nov 23 - Nov 24
Total with taxes and fees
Captain Pips Marina & Hideaway

Courtyard by Marriott Faro Blanco Resort

3.0 star property
Marathon
  • 2 outdoor pools
  • Poolside bar
  • Pool loungers
  • On the beach
  • Hot tub
9.2 out of 10, Wonderful, (1000)
Swimming pools become sanctuaries at this waterfront retreat where 2 outdoor pools feature complimentary cabanas, sun loungers, and a vibrant poolside bar. After refreshing swims, guests savor American cuisine at The Bistro or explore with bicycles and yoga classes.
$186 nightly
The price is $209
Nov 25 - Nov 26
Total with taxes and fees
Courtyard by Marriott Faro Blanco Resort

Sugar Loaf Lodge

2.5 star property
Summerland Key
  • Outdoor pool
8.2 out of 10, Very Good, (1002)
Splash into serenity at the heated outdoor pool overlooking beautiful ocean vistas. This hotel balances aquatic bliss with active pursuits, offering tennis courts, marina access, kayaking, and boat tours, all amid peaceful surroundings praised by guests.
$99 nightly
The price is $111
Nov 23 - Nov 24
Total with taxes and fees
Sugar Loaf Lodge

Parmer's Resort

2.5 star property
Summerland Key
  • Outdoor pool
  • Pool loungers
  • On private beach
9.0 out of 10, Wonderful, (1004)
Floating in the refreshing outdoor pool surrounded by swaying palms creates the perfect complement to days spent exploring the private beach. This waterfront haven offers kayaking, sailing, and boat tours just steps from comfortable, individually furnished rooms.
$137 nightly
The price is $154
Dec 2 - Dec 3
Total with taxes and fees
Parmer's Resort

Isla Bella Beach Resort & Spa

5.0 star property
Marathon
  • 5 outdoor pools
  • Poolside bar
  • Pool loungers
  • On the beach
  • Full-service spa
9.2 out of 10, Wonderful, (1052)
Swimming pools become destinations themselves at this beachfront sanctuary, where five distinct outdoor oases await beneath swaying palms. Pool loungers invite leisurely afternoons while attentive staff deliver refreshing cocktails from the poolside bar.
$296 nightly
The price is $333
Dec 1 - Dec 2
Total with taxes and fees
Isla Bella Beach Resort & Spa

Old Wooden Bridge Resort and Marina

2.5 star property
Punta Brisa
  • Outdoor pool
  • Pool loungers
  • Near the beach
8.6 out of 10, Excellent, (271)
Sparkling waters beckon at this serene fishing retreat, where sun-drenched pool loungers await after kayaking adventures. Marina access, bicycle rentals, and hiking trails create perfect days of outdoor exploration at this peaceful waterfront escape.
$252 nightly
The price is $284
Dec 16 - Dec 17
Total with taxes and fees
Old Wooden Bridge Resort and Marina

Knight's Key Suites

3.0 star property
Marathon
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1155)
Refreshing waters beckon from the inviting outdoor pool where sun loungers provide perfect relaxation spots after exploring nearby bike trails. Clean, comfortable rooms with premium bedding complement this well-maintained retreat near local shops.
$126 nightly
The price is $139
Nov 30 - Dec 1
Total with taxes and fees
Knight's Key Suites

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
  • Near the beach
8.2 out of 10, Very Good, (48)
$286 nightly
The price is $317
Nov 30 - Dec 1
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
  • Outdoor pool
  • Children's pool
  • Hot tub
9.6 out of 10, Exceptional, (99)
$369 nightly
The price is $410
Nov 24 - Nov 25
Total with taxes and fees
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning
9.2 out of 10, Wonderful, (158)
$286 nightly
The price is $317
Nov 24 - Nov 25
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Port Pine Heights Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Port Pine Heights?
Isla Bella Beach Resort & Spa: Hotel located near Sombrero Beach. Features a full-service spa, 5 outdoor pools, and 2 bars. Old Wooden Bridge Resort and Marina: Offers free self parking, an outdoor pool, and complimentary wireless internet access. Courtyard by Marriott Faro Blanco Resort: Hotel located near Sombrero Beach. Provides a full-service spa, 2 outdoor pools, and 2 bars. Tranquility Bay Beachfront Hotel and Resort: Hotel located near Sombrero Beach. Features a private beach, 3 outdoor pools, and spa services. Captain Pips Marina & Hideaway: Hotel located near Sombrero Beach. Offers complimentary bicycles, an outdoor pool, and complimentary wireless internet access.
What is there to see and do in Port Pine Heights?
Enjoy a stroll along the shore at Calusa Beach and Florida Keys Beaches. During your stay, check out sights such as Cook Island, Bahia Honda State Park, and Upper Sugarloaf Key.

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