A coastal road with a beach on one side and a marina with boats on the other.

Find Hotels with a Pool in Summerland Key, FL

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Check availability on Summerland Key Hotels with a Pool

Tonight
Aug 7 - Aug 8
Tomorrow
Aug 8 - Aug 9
This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Our top choices for Summerland Key hotels with a pool

Dock
Suite, 1 Bedroom, Kitchen, Sea Facing | Iron/ironing board (on request), WiFi (free), individually decorated
Private beach, sun loungers, beach umbrellas, beach towels
Suite, 1 Bedroom, Kitchen, Sea Facing | Living area | TV, books, stereo

1. 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.
$129 nightly
$145 total
Aug 11 - Aug 12
Total with taxes and fees
Parmer's Resort
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers
Karaoke room
Sports bar, pool views, open daily
Lunch and dinner served

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$100 nightly
$112 total
Sep 2 - Sep 3
Total with taxes and fees
Looe Key Reef Resort
Outdoor pool
Exterior
Restaurant
Lobby

3. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
$119 nightly
$134 total
Aug 16 - Aug 17
Total with taxes and fees
Sugar Loaf Lodge
Outdoor pool, a heated pool
Exterior
Coffee/tea maker, fridge, microwave, oven
LED TV, DVD player, table tennis, books

4. SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$448 nightly
$497 total
Aug 15 - Aug 16
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool
Interior
Marina
Outdoor dining

5. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
$439 nightly
$487 total
Sep 4 - Sep 5
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A heated pool
Beach
Outdoor dining
Sport court

6. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
$501 nightly
$555 total
Sep 1 - Sep 2
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Exterior detail
TV
Microwave, oven, stovetop
Shower, hair dryer, towels, soap

7. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$542 nightly
$601 total
Aug 17 - Aug 18
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Outdoor pool, a heated pool
Property grounds
Exterior
Property grounds

8. SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$448 nightly
$497 total
Aug 12 - Aug 13
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool
Outdoor dining
Beach
Exterior

9. Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
$578 nightly
$641 total
Aug 14 - Aug 15
Total with taxes and fees
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
A heated pool
Smart TV, table tennis, books
Beach
Outdoor dining

10. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
$554 nightly
$615 total
Aug 16 - Aug 17
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
View all properties

Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Room was small but we booked last minute for lobster season but everything else was great!!"
Mary 2-night trip
Posted 1 day ago
Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"A clean comfortable room, with a lovely view from the back patio! All staff were very helpful."
Marjorie 1-night trip
Posted 10 days ago
Sugar Loaf Lodge

Frequently asked questions

What's it like visiting Summerland Key?
If lounging next to a pool is your idea of a great vacation, you may want to consider Summerland Key, which has 27 places to stay with pools. During your visit, you can explore attractions like Florida Keys Beaches, and then kick back and relax poolside at one of the accommodations in Summerland Key that travelers like for their pools.
What are some accommodations with pools in Summerland Key?
Parmer's Resort: Features a private beach, an outdoor pool, and daily. Sugarloaf Key Hotel at KOA Resort: Offers a private beach, an outdoor pool, and a full-service spa. Sugarloaf Key RV Resort & Cottages: Provides a private beach, an outdoor pool, and a snack bar/deli. Sugar Loaf Lodge: Features free self parking, an outdoor pool, and complimentary wireless internet access. Looe Key Reef Resort: Hotel located near Florida Keys Beaches. Offers 2 outdoor tennis courts, an outdoor pool, and free self parking.
How many hotels with pools will I be able to find in Summerland Key?
Expedia's 27 hotels in Summerland Key give you a great choice for your poolside getaway.
What is there to see and do in Summerland Key?
Explore places like Florida Keys Beaches while you're in Summerland Key. Spend some time experiencing the great outdoors at Upper Sugarloaf Key and Venture Key.
When is the best time to book a hotel with a pool in Summerland Key?
Taking into account the local weather in Summerland Key is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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 73°F. Average annual precipitation for Summerland Key is 35 inches.

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