Summerland Key Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Summerland Key holiday rentals

2 bedrooms, Internet

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is RM2,024
RM3,626 total
includes taxes & fees
14 Jun - 15 Jun
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, (2 reviews)
"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 RM2,230
RM4,070 total
includes taxes & fees
19 Jun - 20 Jun
Atlantic View Luxury Villa with Pool
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, (187 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is RM460
RM1,182 total
includes taxes & fees
8 Jun - 9 Jun
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, (1,199 reviews)
"Good value for money. Would definitely stay again "
Canada
Raghavan
The price is RM356
RM486 total
includes taxes & fees
8 Jun - 9 Jun
Knight's Key Suites
1 bedroom

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is RM1,382
RM1,904 total
includes taxes & fees
4 Jun - 5 Jun
Ocean Front One Bedroom Residence
Living area

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (343 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is RM473
RM1,089 total
includes taxes & fees
17 Jun - 18 Jun
Old Wooden Bridge Resort and Marina
Premium bedding, individually decorated, individually furnished

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is RM1,852
RM4,554 total
includes taxes & fees
4 Jun - 5 Jun
Lighthouse Suites Collection
Exterior

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is RM3,739
RM5,792 total
includes taxes & fees
7 Jun - 8 Jun
Contra House Key West
Exterior

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 RM1,179
RM1,676 total
includes taxes & fees
8 Jun - 9 Jun
Resort View 1BR Suite With Direct Pool Access
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 RM1,518
RM2,811 total
includes taxes & fees
9 Jun - 10 Jun
Poolside Suite by Brightwild Pvt Pool Parking
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 RM1,545
RM3,062 total
includes taxes & fees
4 Jun - 5 Jun
Sea Breeze by Brightwild Off-street Parking
2 bedrooms

Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
The price is RM1,791
RM2,864 total
includes taxes & fees
4 Jun - 5 Jun
Resort View 2BR Residence
Exterior

Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
The price is RM1,921
RM3,235 total
includes taxes & fees
4 Jun - 5 Jun
Ocean Front 2BR Residence
1 bedroom, Internet

New Coastal Rose - Bright Loft With High Ceilings

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
Key West Historic District
The price is RM1,016
RM2,370 total
includes taxes & fees
8 Jun - 9 Jun
New Coastal Rose - Bright Loft With High Ceilings
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 RM2,330
RM3,995 total
includes taxes & fees
8 Jun - 9 Jun
Sky Suite on Duval by Brightwild Condo w Balcony
Terrace/patio

The Collins on Duval by Brightwild

The Collins on Duval by Brightwild
2.0 star property
Old Town Key West
The price is RM2,484
RM4,168 total
includes taxes & fees
8 Jun - 9 Jun
The Collins on Duval by Brightwild
Exterior

Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
The price is RM2,306
RM4,168 total
includes taxes & fees
4 Jun - 5 Jun
Resort View 3BR Residence
2 bedrooms, Internet

Mesa House Dos by Brightwild Unreal Location

Mesa House Dos by Brightwild Unreal Location
2.0 star property
Key West Historic District
The price is RM1,805
RM3,929 total
includes taxes & fees
8 Jun - 9 Jun
Mesa House Dos by Brightwild Unreal Location
Terrace/patio

Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is RM983
RM1,916 total
includes taxes & fees
8 Jun - 9 Jun
Banana Split by Brightwild Pool Grill
Terrace/patio

The Mesa House by Brightwild Close to Duval

The Mesa House by Brightwild Close to Duval
2.0 star property
Key West Historic District
The price is RM3,379
RM6,274 total
includes taxes & fees
11 Jun - 12 Jun
The Mesa House by Brightwild Close to Duval
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Nice and quiet on the water"
Jeffrery 1-night trip
Posted 3 hours ago
Parmer's Resort

Find out more about Summerland Key

Search for holiday rentals in Summerland Key on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Summerland Key using one of the methods below:

  • View our selection of featured holiday rentals in Summerland Key
  • Use the map to find apartments and other holiday homes in the Summerland Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Summerland Key while they last

Look no further and take a look at our great range of rental properties in Summerland Key!

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.

What are some of the best holiday rentals that Summerland Key has to offer?

Sugarloaf Key RV Resort & Cottages: This highly rated holiday home rental in Summerland Key is located near a metro station, and offers an outdoor pool, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Summerland Key?

Choose from 465 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Florida Keys Beaches and Upper Sugarloaf Key are a couple of lovely local spots to get outside and enjoy nature. Sugarloaf Beach and Venture Out Keys 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.