Vacation Homes in Summerland Key, FL
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Vacation Homes in Summerland Key

Sugarloaf Key RV Resort & Cottages

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Private Secluded Ocean View & Pool Near Key West

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

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Kelly's Kabin - Adorable Private Summerland Key Cottage

20 MINUTES TO KEY WEST , BOATERS PARADISE

Keys House - Venture Out Lot 220
Top hotels in Summerland Key

Sugarloaf Key Hotel at KOA Resort
Find the Best Vacation Homes in Summerland Key
Why book a vacation home in Summerland Key?
Vacation homes in Summerland Key make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Summerland Key?
Private Summerland Key rental homes range between $105 - $761 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Summerland Key vacation home rentals. You might look for Summerland Key rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Summerland Key offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Summerland Key?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Summerland Key. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Summerland Key hotels and vacation homes that best suit your stay. We also have deals for flights, and Summerland Key car rentals. You’ll save even more when you bundle your items into a Summerland Key vacation package!
How many vacation homes are available to book in Summerland Key?
There are 392 rental homes in Summerland Key. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Summerland Key?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Summerland Key Vacation Homes essential information
Accommodation | 392 Vacation Homes |
|---|---|
Lowest Price | $105 |
Highest Price | $761 |
Popular accommodation | Sugarloaf Key RV Resort & Cottages, Cudjoe Cottages, swimming pool, just 20 miles from Key West, Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views, Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Private Secluded Ocean View & Pool Near Key West, Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out, Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West, Just 20 miles from Key West! Oceanfront, dockage, swimming pool, Kelly's Kabin - Adorable Private Summerland Key Cottage, 20 MINUTES TO KEY WEST , BOATERS PARADISE, Keys House - Venture Out Lot 220, Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball |
More ways to wander Summerland Key
Explore More Ways to Travel with Travelocity
- Hotels in Marathon
- Southwinds Motel
- The Marquesa Hotel
- Villas in Summerland Key
- The Perry Hotel & Marina Key West
- Caravanparks in Summerland Key
- Southernmost House - Adult Exclusive
- Houseboats in Summerland Key
- The Southernmost Inn - Adults Only
- Hotels in Summerland Key
- Hotels in Key West
- Cottages in Summerland Key
- Houseboats in Key West
- Bedandbreakfast in Summerland Key
- Privatevacationhomes in Key West
- Sugarloaf Key Hotel at KOA Resort
- Resorts in Key West
- Sugar Loaf Lodge
- Hotels near Southernmost Point
- Bedandbreakfast in Little Torch Key
- Resorts in Ramrod Key
- Condos in Little Torch Key
- Motels in Ramrod Key
- Cottages in Little Torch Key
- Looe Key Reef Resort
- Parmer's Resort
- Old Town Key West Hotels
- Caravanparks in Little Torch Key
- Resorts in Melody Key
- Lime Tree Bay Resort
- Cabins in Melody Key
- Apartments in Lower Keys
- Houseboats in Marathon
- Houseboats in Lower Keys
- Motels in Lower Keys
- Privatevacationhomes in Lower Keys
- Banana Bay Resort & Marina
- Beach in Marathon
- Coconut Cay Resort & Marina
- Conch Key Fishing Lodge and Marina
- Faro Blanco Resort Marathon Florida Keys Curio by Hilton
- Hawks Cay Resort
- Isla Bella Beach Resort & Spa
- Tranquility Bay Beachfront Hotel and Resort
- Skipjack Resort & Marina
- Resorts in Bahia Honda Key
- Old Wooden Bridge Resort and Marina
- Sunshine Key RV Resort & Marina
- Hotels in Big Pine Key
- Motels in Big Pine Key
- Resorts in Big Pine Key
- Casa Marina Hotels
- Bedandbreakfast in Cudjoe Key
- Cottages in Cudjoe Key
- Caravanparks in Cudjoe Key
- Villas in Cudjoe Key
- Hotels near Duval Street
- Cheeca Lodge & Spa
- Hotels in Islamorada
- Bedandbreakfast in Key West
- Condos in Key West
- Key West Historic District Hotels
- Adults Only in Key West
- All-Inclusive in Key West
- Amsterdam's Curry Mansion Inn
- Beach in Key West
- Casa Marina Key West Curio Collection by Hilton
- Budget in Key West
- Coconut Beach Resort
- Duval House
- H2O Suites - Adults Only
- Havana Cabana at Key West
- Heron House - Adult Only
- The Independent Inn - Formerly Heron House Court
- Island City House Hotel
- Beachside Resort & Residences
- Lighthouse Hotel - Key West Historic Inns
- Winslow's Bungalows - Key West Historic Inns
- NYAH Key West - Adults Only
- Ocean Key Resort - A Noble House Resort
- Hilton Key West Resort & Marina
- Opal Key Resort & Marina Key West
- Parrot Key Hotel & Villas
- Pier House Resort & Spa
- Silver Palms Inn & Historic Homes
- Simonton Court Historic Inn & Cottages
- Southernmost Beach Resort and Guesthouses






