Summerland Key houses
We found 668 houses — enter your dates for availability
Explore Summerland Key house rentals

Sugarloaf Key RV Resort & Cottages
Sleeps 4 · 1 bedroom · 1 bathroom

One of the very few beach houses with a daily, rental license in the Keys.
Sleeps 12 · 4 bedrooms · 3 bathrooms

Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
Sleeps 10 · 3 bedrooms · 2 bathrooms

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Sleeps 6 · 2 bedrooms · 2 bathrooms

Ocean Breeze House - Summer fun Sleeps 8 boating, fishing and 🦞 Lobster season.
Sleeps 8 · 2 bedrooms · 2 bathrooms

Private Secluded Ocean View & Pool Near Key West
Sleeps 10 · 4 bedrooms · 2 bathrooms
Find spaces that suit your style
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- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any holiday home rentals in Summerland Key?
Pick one of our 668 holiday home rentals and start planning your Summerland Key trip. Whether you're going to stay in Cutthroat Harbour Estates, Breezeswept Beach Estates, Cudjoe Gardens or another well-known area, you'll discover the perfect house on Bookabach.
How much does it cost to stay in a holiday rental house in Summerland Key?
Prices vary according to season, length of stay and specific location, so key in your travel details to discover what's available. Whatever your budget or style, Bookabach has holiday home rentals in Summerland Key for guests of every type.
Where can I rent a Summerland Key holiday house with great views?
When looking for your holiday home rental in Summerland Key, use the "Location" filter. This will help you choose the types of areas you'd like to stay in, whether that's around nature or somewhere more central.
Does Summerland Key have any weekend house rentals?
You'll discover a range of comfortable houses that are available for weekend rental. Simply key in your preferred dates of travel and look forward to a fun-packed few days away. If you can't see the perfect holiday home rental in Summerland Key right away, just modify your dates and search again.
Are there any pet-friendly house rentals in Summerland Key?
With 60 pet-friendly holiday home rentals in Summerland Key, you can plan your next getaway with your furry companion by your side. In addition to a comfy bed for everyone, plenty of houses also include perks like fenced-in yards and complimentary dog treats. See what's available by choosing the "Pets allowed" filter.
What are the top things to do in Summerland Key?
It's no surprise why many families love Summerland Key, with cool attractions like Bahia Honda State Park, Florida Keys Beaches and Calusa Beach to explore. Discover this destination's best sights together and then return to the cosy comforts of your holiday home rental.
Why should I book my holiday rental house with Bookabach?
Bookabach takes the hassle out of finding your perfect holiday home rental. Use our filters to fine-tune your search by property type, nightly price, features and more. Whatever your preference, you'll always get the entire property for you and whoever you're getting away with. Plus, our cancellation policies offer peace of mind should your plans change. You'll get a 100% refund if you cancel your booking within the timeframe specified by the property's cancellation policy.
