Search Holiday Rentals in Summerland Key

Start date: Check-in selected.
To Date
End date: Check-out

    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

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Top Holiday Rentals in Summerland Key

Premium bedding, soundproofing, iron/ironing board, free WiFi
Knight's Key Suites
Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1151)
"Room were clean and staff was very helpful "
United States
Leonard
The price is ฿2,527
฿3,549 total
includes taxes & fees
21 Oct - 22 Oct
Knight's Key Suites
Restaurant
Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (164)
"The stay was beautiful "
United States
Jennifer
The price is ฿2,926
฿8,797 total
includes taxes & fees
21 Oct - 22 Oct
Aqua Lodges at Hurricane Hole Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV
Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (260)
"I love this place!!!"
United States
Greg
The price is ฿3,127
฿8,136 total
includes taxes & fees
26 Oct - 27 Oct
Old Wooden Bridge Resort and Marina
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very good, (314)
"Great hotel with excellent location "
United States
Rony
The price is ฿7,856
฿9,947 total
includes taxes & fees
20 Nov - 21 Nov
Hyatt Vacation Club at Sunset Harbor, Key West
Apartment | 2 bedrooms, Internet
The Grenada Suite Pool View Private Balcony
The Grenada Suite Pool View Private Balcony
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is ฿9,804
฿20,008 total
includes taxes & fees
22 Oct - 23 Oct
The Grenada Suite Pool View Private Balcony
Exterior
Coconut Mallory Marina and Resort Condo
Coconut Mallory Marina and Resort Condo
3.0 star property
The price is ฿32,484
฿43,113 total
includes taxes & fees
24 Oct - 25 Oct
Coconut Mallory Marina and Resort Condo
Exterior
Contra House Key West
Contra House Key West
3.0 star property
The price is ฿37,735
฿55,589 total
includes taxes & fees
27 Oct - 28 Oct
Contra House Key West
Apartment | 2 bedrooms, Internet
The Trinidad by Brightwild Pool View Parking
The Trinidad by Brightwild Pool View Parking
2.0 star property
10.0 out of 10, Exceptional, (1)
"Our family spent one night at Key West and we fully enjoyed our stay here. Room is very clean, stylish and spacious. Beds are comfortable."
United States
Xiulin
The price is ฿11,881
฿22,344 total
includes taxes & fees
18 Nov - 19 Nov
The Trinidad by Brightwild Pool View Parking
Apartment | 2 bedrooms
Grand Marina Suite by Brightwild Waterfront
Grand Marina Suite by Brightwild Waterfront
2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
The price is ฿14,534
฿24,331 total
includes taxes & fees
22 Oct - 23 Oct
Grand Marina Suite by Brightwild Waterfront
Apartment | 1 bedroom
Island View 1BR Residence With Balcony
Island View 1BR Residence With Balcony
2.0 star property
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
The price is ฿8,728
฿12,612 total
includes taxes & fees
21 Oct - 22 Oct
Island View 1BR Residence With Balcony
Apartment | 1 bedroom, Internet
The Bartlum Luxury Studio In Prime Location
The Bartlum Luxury Studio In Prime Location
2.0 star property
The Bartlum Luxury Studio In Prime Location
Apartment | 1 bedroom, Internet
New Coastal Rose - Bright Loft With High Ceilings
New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
The price is ฿13,957
฿25,678 total
includes taxes & fees
18 Nov - 19 Nov
New Coastal Rose - Bright Loft With High Ceilings
Apartment | 1 bedroom, Internet
Banana Split by Brightwild Pool Grill
Banana Split by Brightwild Pool Grill
2.0 star property
Banana Split by Brightwild Pool Grill
Apartment | 2 bedrooms, Internet
Poolside Suite by Brightwild Pvt Pool Parking
Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Poolside Suite by Brightwild Pvt Pool Parking
Apartment | 1 bedroom, Internet
Mesa House Uno by Brightwild Perfect Location
Mesa House Uno by Brightwild Perfect Location
2.0 star property
The price is ฿22,493
฿31,290 total
includes taxes & fees
22 Oct - 23 Oct
Mesa House Uno by Brightwild Perfect Location
Apartment | 1 bedroom, Internet
Sky Loft by Brightwild Penthouse in Prime Spot
Sky Loft by Brightwild Penthouse in Prime Spot
2.0 star property
The price is ฿21,109
฿29,733 total
includes taxes & fees
22 Oct - 23 Oct
Sky Loft by Brightwild Penthouse in Prime Spot
Apartment | 2 bedrooms, desk, Internet
Duval Dream Loft by Brightwild Right on Duval
Duval Dream Loft by Brightwild Right on Duval
2.0 star property
10.0 out of 10, Exceptional, (1)
Duval Dream Loft by Brightwild Right on Duval
Apartment | 2 bedrooms, Internet
Sea Breeze by Brightwild Off-street Parking
Sea Breeze by Brightwild Off-street Parking
2.0 star property
The price is ฿11,727
฿23,767 total
includes taxes & fees
29 Oct - 30 Oct
Sea Breeze by Brightwild Off-street Parking
Apartment | 2 bedrooms, Internet
The Grand Turk by Brightwild Sunset View Pool
The Grand Turk by Brightwild Sunset View Pool
2.0 star property
The price is ฿9,843
฿20,052 total
includes taxes & fees
22 Oct - 23 Oct
The Grand Turk by Brightwild Sunset View Pool
Apartment | 1 bedroom, Internet
Road s End by Brightwild Steps to Duval St
Road s End by Brightwild Steps to Duval St
2.0 star property
10.0 out of 10, Exceptional, (1)
"Property was very clean with a great location. The also supported us with an early check in. Would recommend "
United States
RIAAN
Road s End by Brightwild Steps to Duval St
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

Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"We enjoyed our three night stay. We dived Looe Key reef every day through their dive shop. Safe shallow diving with excellent storage, easy access and excellent staff. Left the afternoon/evening open to relax or go into town. About 50 minutes from Key West. Recommend car rental for your stay"
Timothy 4-night trip
Posted 3 days 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:

  • 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.

How many holiday rentals are there in Summerland Key?

Choose from 492 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Sugarloaf Beach and Venture Out Keys are a couple of lovely local spots to get outside and enjoy nature. Upper Sugarloaf Key and Coupon Bight Aquatic Preserve 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.