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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Summerland Key holiday rentals

House | 2 bedrooms, Internet

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is 13.152.262 ₫
24.112.782 ₫ total
includes taxes & fees
12 Mar - 13 Mar
Starlight Serenity - Hideaway w Stunning Views
Exterior

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is 14.729.625 ₫
26.881.567 ₫ total
includes taxes & fees
15 Mar - 16 Mar
Atlantic View Luxury Villa with Pool
Studio, Non Smoking (Tiny House Isla) | Living area | TV, fireplace

Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina
2.0 star property
Big Pine Key
8.8 out of 10, Excellent, (160 reviews)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
The price is 7.986.730 ₫
8.985.202 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Sunshine Key RV Resort & Marina
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (180 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is 5.372.615 ₫
10.413.841 ₫ total
includes taxes & fees
8 Mar - 9 Mar
Aqua Lodges at Hurricane Hole Marina
Premium bedding, soundproofing, iron/ironing board, free WiFi

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,174 reviews)
"Very a nice place clean nice location good price"
United States
Pawel
The price is 4.651.943 ₫
5.796.271 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Knight's Key Suites
Apartment | 1 bedroom

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is 15.871.509 ₫
20.226.918 ₫ total
includes taxes & fees
1 Mar - 2 Mar
Ocean Front One Bedroom Residence
1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (304 reviews)
"Great stay in Bug Pine Key! Clean and spacious room, excellent staff and Beautiful views!"
United States
Peter
Old Wooden Bridge Resort and Marina
Exterior

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
The price is 30.951.852 ₫
45.295.234 ₫ total
includes taxes & fees
3 Mar - 4 Mar
Contra House Key West
House (2 Bedrooms) | Interior

Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool

Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
4.0 star property
Stock Island
7.4 out of 10, Good, (3 reviews)
"Excelente "
Mexico
Wilfredo
The price is 14.114.254 ₫
29.570.900 ₫ total
includes taxes & fees
6 Mar - 7 Mar
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
Apartment | Terrace/patio

Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
The price is 15.954.606 ₫
25.571.512 ₫ total
includes taxes & fees
3 Mar - 4 Mar
Poolside Suite by Brightwild Pvt Pool Parking
Apartment | 2 bedrooms, Internet

Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
The price is 21.060.119 ₫
32.670.341 ₫ total
includes taxes & fees
23 Mar - 24 Mar
Sea Breeze by Brightwild Off-street Parking
Exterior

Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
The price is 11.598.349 ₫
18.129.863 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Mesa House Uno by Brightwild Perfect Location
Apartment | 2 bedrooms, Internet

Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is 14.789.271 ₫
24.260.510 ₫ total
includes taxes & fees
23 Mar - 24 Mar
Tortuga Suite Sparkling Pool Hot Tub
Interior

Sky Suite on Duval by Brightwild Condo w Balcony

Sky Suite on Duval by Brightwild Condo w Balcony
2.0 star property
Old Town Key West
The price is 20.754.838 ₫
32.665.680 ₫ total
includes taxes & fees
24 Mar - 25 Mar
Sky Suite on Duval by Brightwild Condo w Balcony
Apartment | 4 bedrooms, Internet

Commodore s Cove by Brightwild Epic Location

Commodore s Cove by Brightwild Epic Location
2.0 star property
Key West Historic District
The price is 33.768.406 ₫
53.234.619 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Commodore s Cove by Brightwild Epic Location
Apartment | 1 bedroom

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is 11.820.337 ₫
15.669.349 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Resort View 1BR Suite With Direct Pool Access
Apartment | 3 bedrooms

Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
The price is 21.809.376 ₫
35.207.161 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Resort View 3BR Residence
Apartment | 2 bedrooms

Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
The price is 21.226.709 ₫
31.163.846 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Ocean Front 2BR Residence
Apartment | 1 bedroom, Internet

The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is 11.071.080 ₫
17.536.685 ₫ total
includes taxes & fees
2 Mar - 3 Mar
The Bartlum Luxury Studio In Prime Location
House | 3 bedrooms, Internet

Poolside Paradise by Brightwild Heated Pool

Poolside Paradise by Brightwild Heated Pool
2.0 star property
Old Town Key West
The price is 42.231.232 ₫
60.214.439 ₫ total
includes taxes & fees
23 Mar - 24 Mar
Poolside Paradise by Brightwild Heated Pool
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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"What a wonderful place to stay. Very beautiful and tranquil. If you are looking for things to do, it is there. Everyone there was extremely helpful and was quick to go out of their way to make sure your stay was enjoyable. "
Kathryn A 5-night trip
Posted 2 days ago
Parmer's Resort

Frequently asked questions

Can I find holiday rentals in Summerland Key?

Yes, there are holiday rentals close to the most popular sights in Summerland Key, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Summerland Key?

Choose from 471 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Florida Keys Beaches and Sugarloaf Beach are a couple of lovely local spots to get outside and enjoy nature. Venture Out Keys and Upper Sugarloaf Key are other places to visit while you're in town.

What are holiday rentals like in Summerland Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Summerland Key. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.