Summerland Key Vacation Rentals from AED 1,416: Search Short-Term Rentals

Q: What's the top vacation rental in Summerland Key?

Sugarloaf Key RV Resort & Cottages : This Summerland Key vacation home rental 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 vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Summerland Key is Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball .

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In two weeks

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Our top choices for Summerland Key vacation rentals

1. Starlight Serenity - Hideaway w Stunning Views

Summerland Key

max

AED 2,245 total

includes taxes & fees

30 Sep - 1 Oct

2. Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

AED 3,585 total

includes taxes & fees

3 Oct - 4 Oct

Premium bedding, soundproofing, iron/ironing board, WiFi (free)

3. Knight's Key Suites

Marathon

chantal

AED 363 total

includes taxes & fees

29 Sep - 30 Sep

4. Ocean Front One Bedroom Residence

Key West

AED 1,199 total

includes taxes & fees

30 Sep - 1 Oct

1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

5. Old Wooden Bridge Resort and Marina

Punta Brisa

Daisybel

AED 888 total

includes taxes & fees

29 Sep - 30 Sep

Condo | Living area | 32-inch Smart TV with satellite channels

6. Coconut Mallory Marina and Resort Condo

Key West

Paris

7. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

AED 984 total

includes taxes & fees

30 Sep - 1 Oct

Outdoor pool, pool umbrellas, sun loungers

8. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Marathon

Arianna

AED 641 total

includes taxes & fees

30 Sep - 1 Oct

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Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Nice place and clean, lots to do."

Waterfront 2BR, Dock,Golf Cart, trailer parking,Open Water Views Venture Out 320

10/10 Excellent

"Our three-night stay at this exceptional waterfront retreat was nothing short of extraordinary. Set against sweeping open-water views, the property offers that rare combination of effortless comfort, understated elegance, and a truly idyllic setting.From the moment we arrived, the home felt like a private escape designed for relaxation. The interiors were inviting and beautifully maintained, while the waterfront setting provided a spectacular backdrop throughout our stay. Mornings overlooking the water and quiet evenings by the dock were among the many memorable moments.The private dock and golf cart elevated the experience even further, making it wonderfully easy to explore the community and enjoy everything the resort has to offer. Every detail seemed to encourage slowing down, savoring the surroundings, and simply enjoying being there.Although we stayed only three nights, the experience felt wonderfully restorative—and we found ourselves wishing we had booked a much longer stay. This is the kind of place where the pace immediately changes, the views become part of the experience, and a short getaway feels like a true escape.Beautifully situated, exceptionally comfortable, and surrounded by breathtaking waterfront scenery, this home is a destination in itself. We would return without hesitation and look forward to our next visit. A truly memorable stay in a spectacular setting. Host Mel is wonderful and very attentive."

Ocean Breeze House - Summer fun Sleeps 8 boating, fishing and 🦞 Lobster season.

10/10 Excellent

"Glen was more than helpful with our visit. He was very prompt and knowledgeable with the area. The property is very large and tranquil. The house was very spacious and accommodating. We would recommend this property!!"

Direct Oceanfront Cottage-Sunrise View- #2,

10/10 Excellent

"Delightful cottage. It can get a little warm without central AC but the window units do a pretty good job of cooling it down. The kitchen doesn’t have a unit and had I actually wanted to cook I imagine it might be too hot. But if you’re not planning to cook and just need a nice comfortable space for o relax after a full day on and in the water this is it! We will definitely be looking to come back next year."

Frequently asked questions

Can I find vacation rentals in Summerland Key?

Yes, you can find vacation rentals close to top local attractions in Summerland Key, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Summerland Key?

Sugarloaf Key RV Resort & Cottages: This Summerland Key vacation home rental 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 vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Summerland Key is Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball.

How many vacation rentals are there in Summerland Key?

Choose from 481 Expedia vacation rentals in Summerland Key for a memorable vacation.

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 vacation rentals like in Summerland Key?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Summerland Key. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.

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Check prices for these dates

Our top choices for Summerland Key vacation rentals

1. Starlight Serenity - Hideaway w Stunning Views

2. Atlantic View Luxury Villa with Pool

3. Knight's Key Suites

4. Ocean Front One Bedroom Residence

5. Old Wooden Bridge Resort and Marina

6. Coconut Mallory Marina and Resort Condo

7. Aqua Lodges at Hurricane Hole Marina

8. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

9. Contra House Key West

10. Resort View 1BR Suite With Direct Pool Access

11. Sea Breeze by Brightwild Off-street Parking

12. Island View 1BR Residence With Balcony

13. Resort View 3BR Residence

14. Sky Suite on Duval by Brightwild Condo w Balcony

15. Poolside Suite by Brightwild Pvt Pool Parking

16. Resort View 2BR Residence

17. Ocean Front 2BR Residence

18. The Collins on Duval by Brightwild

19. Grand Marina Suite by Brightwild Waterfront

20. NEW The Rigby House - Pvt Pool Amazing Location

Find vacation rentals that suit your style

Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Looe Key Reef Resort

Sugar Loaf Lodge

Waterfront 2BR, Dock,Golf Cart, trailer parking,Open Water Views Venture Out 320

Sugarloaf Key RV Resort & Cottages

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

Ocean Breeze House - Summer fun Sleeps 8 boating, fishing and 🦞 Lobster season.

Direct Oceanfront Cottage-Sunrise View- #2,

Cottage with Pool and Dockage, just minutes to Key West

Frequently asked questions

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