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

Summerland Key Hotel Guide - Hotels with Pool in Summerland Key, Florida

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Check availability on Summerland Key Hotels with Pool

Tonight
2 Sept - 3 Sept
Tomorrow
3 Sept - 4 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Summerland Key hotels with a pool

Dock
Exterior
Suite, 1 Bedroom, Kitchen, Sea Facing | Living area
Private beach, sun-loungers, beach umbrellas, beach towels

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.
€173
includes taxes & fees
22 Sept - 23 Sept
Parmer's Resort
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers
Lunch and dinner served
Karaoke room
Sports bar, poolside views, open daily

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
€73
includes taxes & fees
7 Sept - 8 Sept
Looe Key Reef Resort
Outdoor pool
Lobby
Exterior
Restaurant

3. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
€98
includes taxes & fees
7 Sept - 8 Sept
Sugar Loaf Lodge
Outdoor pool, a heated pool
Outdoor dining
Exterior
Coffee/tea maker, fridge, microwave, oven

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
€349
includes taxes & fees
3 Sept - 4 Sept
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool, a heated pool
Exterior
Property grounds
Exterior

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
€370
includes taxes & fees
3 Sept - 4 Sept
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool
Beach
Marina
Outdoor dining

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

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
€438
includes taxes & fees
4 Sept - 5 Sept
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A heated pool
Coffee/tea maker, fridge, microwave, oven
Terrace/patio
Dining

7. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
€325
includes taxes & fees
9 Sept - 10 Sept
Canal Front home with easy Ocean access
Exterior detail
Shower, hair dryer, towels, soap
2 bedrooms, WiFi, bed sheets
Microwave, oven, stovetop

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
€507
includes taxes & fees
14 Sept - 15 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A heated pool
Outdoor dining
Coffee/tea maker, fridge, microwave, oven
Sports court

9. 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
€474
includes taxes & fees
14 Sept - 15 Sept
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A heated pool
Sports court
Terrace/patio
Dining

10. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
€488
includes taxes & fees
10 Sept - 11 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
4 stars
Hot tub
5 stars
Spa

Hotels with pools and hot tubs in Summerland Key

Exterior
2 bedrooms, iron/ironing board, WiFi, bed sheets
Outdoor pool, a heated pool
Coffee/tea maker, fridge, microwave, oven

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
€349
includes taxes & fees
3 Sept - 4 Sept
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Beach
A heated pool
Marina
Outdoor dining

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
€438
includes taxes & fees
4 Sept - 5 Sept
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Terrace/patio
Property grounds
Coffee/tea maker, fridge, microwave, oven
Smart TV, DVD player, ping pong, books

Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
€325
includes taxes & fees
9 Sept - 10 Sept
Canal Front home with easy Ocean access
Exterior detail
Miscellaneous
2 bedrooms, WiFi, bed sheets
Microwave, oven, stovetop

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
€507
includes taxes & fees
14 Sept - 15 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A heated pool
Outdoor dining
Coffee/tea maker, fridge, microwave, oven
Sports court

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
€474
includes taxes & fees
14 Sept - 15 Sept
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Property grounds
Property grounds
Property grounds
Property grounds

Venture Out RV lot 223

Venture Out RV lot 223
Cudjoe key
€204
includes taxes & fees
14 Sept - 15 Sept
Venture Out RV lot 223
Exterior
Property grounds
Terrace/patio
Miscellaneous

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
€232
includes taxes & fees
14 Sept - 15 Sept
Seabreeze Escape WF RV Lot 489
A heated pool
Sports court
Terrace/patio
Dining

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
€488
includes taxes & fees
10 Sept - 11 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Beach
Marina
Outdoor dining
A heated pool

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
€526
includes taxes & fees
3 Sept - 4 Sept
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Beach
Outdoor dining
A heated pool
Exterior

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
€527
includes taxes & fees
10 Sept - 11 Sept
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
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.
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Top Summerland Key Hotel Reviews

Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"Everything was great! Staff was very friendly! Easy check in and check out."
christine 4-night trip
Posted 6 days ago
Looe Key Reef Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Me gustaría más opciones como un regular desayuno"
Susana 2-night trip
Posted 9 days ago
Sugar Loaf Lodge

Frequently asked questions

What's it like visiting Summerland Key?
If taking it easy by the pool is your idea of a great getaway, you may want to look at Summerland Key, which has 27 places to stay with pools. During your visit, you can explore attractions such as Florida Keys Beaches, and then relax and unwind poolside at one of the accommodation options in Summerland Key that travellers like for their pools.
What are some accommodation options 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 can I expect 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 such as Florida Keys Beaches while you're in Summerland Key. Spend some time experiencing the great outdoors at Upper Sugarloaf Key and Pye Key.
When is the best time to book a hotel with a pool in Summerland Key?
Taking the local weather in Summerland Key into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 23°C. Average annual precipitation for Summerland Key is 895 mm.