Summerland Key Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

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 HK$3,879
HK$7,225 total
includes taxes & fees
14 May - 15 May
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 HK$4,406
HK$8,041 total
includes taxes & fees
2 May - 3 May
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, (183 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 HK$1,022
HK$2,463 total
includes taxes & fees
3 May - 4 May
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, (1,189 reviews)
"Ocean view from room balcony."
United States
Brian
The price is HK$817
HK$1,088 total
includes taxes & fees
6 May - 7 May
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 HK$3,732
HK$4,927 total
includes taxes & fees
27 May - 28 May
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, (332 reviews)
"I love the place, for the next time I will stay for more days "
United States
Kenia
The price is HK$909
HK$2,125 total
includes taxes & fees
21 May - 22 May
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 HK$7,387
HK$11,443 total
includes taxes & fees
5 May - 6 May
Contra House Key West
Iron/ironing board, free WiFi

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is HK$4,034
HK$9,422 total
includes taxes & fees
3 May - 4 May
Lighthouse Suites Collection
Interior

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (6 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
The price is HK$1,750
HK$4,482 total
includes taxes & fees
18 May - 19 May
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
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 HK$2,756
HK$5,441 total
includes taxes & fees
31 May - 1 Jun
Poolside Suite by Brightwild Pvt Pool Parking
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 HK$2,838
HK$3,921 total
includes taxes & fees
12 May - 13 May
Resort View 1BR Suite With Direct Pool Access
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 HK$2,867
HK$5,982 total
includes taxes & fees
17 May - 18 May
Sea Breeze by Brightwild Off-street Parking
2 bedrooms

New Rose Retreat - Pool Parking

New Rose Retreat - Pool Parking
2.0 star property
Key West Historic District
The price is HK$3,612
HK$7,965 total
includes taxes & fees
5 May - 6 May
New Rose Retreat - Pool Parking
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 HK$2,457
HK$5,365 total
includes taxes & fees
11 May - 12 May
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 HK$4,230
HK$7,618 total
includes taxes & fees
5 May - 6 May
Sky Suite on Duval by Brightwild Condo w Balcony
2 bedrooms, Internet

Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is HK$2,084
HK$4,684 total
includes taxes & fees
11 May - 12 May
Tortuga Suite Sparkling Pool Hot Tub
2 bedrooms, desk, Internet

Kamp by Brightwild Rooftop Penthouse On Duval

Kamp by Brightwild Rooftop Penthouse On Duval
2.0 star property
Old Town Key West
The price is HK$5,253
HK$8,770 total
includes taxes & fees
5 May - 6 May
Kamp by Brightwild Rooftop Penthouse On Duval
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 HK$2,773
HK$4,679 total
includes taxes & fees
1 Jun - 2 Jun
Mesa House Uno by Brightwild Perfect Location
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 HK$5,191
HK$10,519 total
includes taxes & fees
1 Jun - 2 Jun
Commodore s Cove by Brightwild Epic Location
Exterior

Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
The price is HK$5,460
HK$9,418 total
includes taxes & fees
12 May - 13 May
Resort View 3BR Residence
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

8/10 Good
"Staf at the bar were very dlow"
Haley 6-night trip
Posted 9 hours ago
Looe Key Reef Resort

Find out more about Summerland Key

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

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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. Other favourite homes for rent in Summerland Key are Old Florida Style, wrap around porch, boat basin for dockage, open water and Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill.

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