Summerland Key Holiday Rentals: Short-Term Accommodations for Rent

Q: 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 Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out and Old Florida Style, wrap around porch, boat basin for dockage, open water .

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Summerland Key holiday rentals

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key

Kasey M.

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key

Anthony

HK$2,930 total

includes taxes & fees

16 Jun - 17 Jun

Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

HK$8,916 total

includes taxes & fees

21 Jun - 22 Jun

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

Cudjoe Key

Moriah W.

HK$3,416 total

includes taxes & fees

20 Jun - 21 Jun

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cudjoe Key

Bryan M.

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Cudjoe Key

HK$4,711 total

includes taxes & fees

16 Jun - 17 Jun

Waterfront Home

Cudjoe Key

Karen H.

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key

Sharon L.

HK$3,912 total

includes taxes & fees

17 Jun - 18 Jun

View all properties

Find holiday rentals that suit your style

Aparthotels

Condos

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

Sugarloaf Key RV Resort & Cottages

10/10 Excellent

"First time staying here it won’t be our last!"

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"The property was very clean and well laid out. Lot of great design thought went into the landscape architecture. That also applied to the rooms as well. From great lighting to a bathroom that was spacious, we felt quite at home. (Apparently, we are meant to stay in semi darkness and have a tiny shower and toilet 6 inches from the ground in the vast majority of high-priced chain hotels!) In terms of amenities, it was perfect for us. Pool, food and bar were great as was the marina where we rented a boat for the day. However the highest praise must go to the staff. They were genuinely caring and extremely friendly. Thank you for making this the best time for us."

Parmer's Resort

10/10 Excellent

"Parmer’s Resort on Little Torch Key is the kind of place you go when you truly want to slow down and unwind—but still have everything you need within reach. The property has a classic“old Florida” charm that is not flashy or overdone—instead, it feels cozy, laid-back, and genuinely welcoming. Parmer's has that homey, relaxed vibe that makes it easy to settle in, unplug, and enjoy the simple pleasures of the Keys. It’s the perfect setting if you’re looking to escape the hustle and just breathe for a while. It’s tucked away in a quiet spot, giving you that “away-from-it-all” feeling, yet you’re still just a short drive from great food and local favorites. Places like Kiki’s, Square Grouper, and Tonio’s are all nearby, and there’s even a fun little taco spot a few miles down the road that’s worth checking out. The amenities really add to the experience without feeling overwhelming. There’s a small private beach where you can relax by the water, plus bicycles, kayaks, and stand-up paddleboards available so you can explore at your own pace. It’s easy to fill your day with outdoor activities—or do nothing at all, which is just as enjoyable here. [parmersresort.com] Another highlight is the daily breakfast, which is such a nice touch. Having that ready each morning makes the stay even more convenient. We will be back!!!"

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

8/10 Good

"The property is on a beautiful view of water, and the communication by the host was excellent. Distance from Key West was good and allowed you to be a little outside of the fray. Three pieces of constructive feedback. We stay a lot in Vrbo‘s and the general expectation is that there is sufficient things like toilet paper, paper towel, dishwasher detergent and coffee pods for a Keurig machine that is there. These were not included, other than a starter roll of TP and paper towel. While it apparently says that in the listing, we didn’t catch it because we have grown accustomed to just having it stocked. Given the price, that would be a simple audition and would make a big difference. Labeling the three remotes in the living room, would’ve been helpful. We never could figure out the TV. And last, the golf cart is a big bonus, especially when you have aging people with you. However, the golf cart is in bad shape, it’s old and the brake needs to be fixed. Other than that, it was worth the stay."

SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!

8/10 Good

"The bed was overly soft. Making sleeping a challenge. The area and the pool were great. I never did find the beach with in a 6 minute walk. Room was clean could use a comfortable chair to sit in. All in all it was a great place to stay."

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

8/10 Good

"We enjoyed the location away from the congestion of Key West. The property is a bit tired, but everything was clean and we had what we needed. The grounds had some broken picnic tables and lounge chairs; items the maintenance crew should have removed for safety reasons months ago. This cottage is great for fishermen and those needing water access; also a quiet spot for our small dog. Nothing fancy, but a good value for the Keys."

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.

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 Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out and Old Florida Style, wrap around porch, boat basin for dockage, open water.

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. Sugarloaf Beach and Crab 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Summerland Key holiday rentals

Cottage with Pool and Boat Dockage just minutes to Key West!

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Atlantic View Luxury Villa with Pool

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

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Waterfront Home

Kelly's Kabin - Adorable Private Summerland Key Cottage

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Canalfront Keys Home - Dock for 35' Boat, Large Porch, Big Yard & Quick Access to Open Water

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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

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

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Seabreeze Escape WF RV Lot 489

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Starlight Serenity - Hideaway w Stunning Views

Endless Ocean Views - RV589

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

Find holiday rentals that suit your style

Top Summerland Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key Hotel at KOA Resort

Oceanside Paradise in the FL Keys Free Kayaks Bikes Community Pool & Hot Tub

Parmer's Resort

Sugar Loaf Lodge

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

Looe Key Reef Resort

SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Find out more about Summerland Key

Frequently asked questions

Go further with the Expedia app