Choose from 310 vacation rentals located in Summerland Key, Florida. Top filters in Summerland Key include Internet / Wifi, Air conditioner, and Laundry. Prices range from $39 to $2,502 per night. Our most popular vacation rental types near Summerland Key are Condo and Hotel.

Top vacation rentals in Summerland Key

Front / Side View of home
4.8
Outstanding(212 Reviews)
House
 in Cudjoe Key
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

This House for $150 in Summerland Key, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Welcome to Tidewater Views...
4.9
Outstanding(192 Reviews)
Cottage
 in Cudjoe Key
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
6 guests · 2 bedrooms · 2 baths
Pool · Pets allowed · Kitchen / Kitchenette

Indulge in a peaceful retreat at **TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool, our elegant Cottage in Summerland Key. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Beachfront
Property view
House
 in Cudjoe Key
Parrotfish Pointe
Pool · Kitchen / Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our House in Summerland Key has everything you need for a rejuvenating stay. Treat yourself to Parrotfish Pointe's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$
booking logo
View deal
Beachfront
Property view
4.7
Outstanding(4 Reviews)
House
 in Cudjoe Key
Pelican's Roost, Waterfront comfort at Venture Out
Garden · Pool · Kitchen / Kitchenette

The best choice in Summerland Key for House, for $174 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal

Search by amenity

Explore vacation rentals with the most popular amenities in Summerland Key

Vacation rentals with internet & wifi in Summerland Key

Exterior
4.8
Outstanding(169 Reviews)
House
 in Cudjoe
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Experience vacation in Summerland Key with our House, Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Property view
House
 in Cudjoe Key
Hawkins Lookout
Pets allowed · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Summerland Key? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
booking logo
View deal
Property view
House
 in Summerland Key
Summerland Canal
Pool · Kitchen / Kitchenette · Air conditioner

Experience the best of Summerland Key with this House available for $78. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
booking logo
View deal
Property view
House
 in Cudjoe Key
The Blue Marlin
Garden · Pets allowed · Kitchen / Kitchenette

Experience vacation in Summerland Key with our House, The Blue Marlin. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
booking logo
View deal
city photo
Summerland Key

Summerland Key travel guide

Let us help you plan your perfect Summerland Key vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Summerland Key, and more.

Frequently asked questions

What is the price range for rentals in Summerland Key?

Vacation rentals in Summerland Key have a price range between $39-$2,502. The average price for rentals in Summerland Key is $275 per night.

What do I need to know before visiting Summerland Key, FL?

Before visiting Summerland Key, FL, it's important to know about the local climate, water activities, and the rules and regulations for visiting the area. Here's a quick summary:

  • The climate in Summerland Key is mostly hot and humid, with temperatures ranging from the low 60s in the winter, to the mid-80s in the summer.
  • The island is a great destination for water activities, such as kayaking, paddle-boarding, and swimming.
  • Please be aware of the rules and regulations set by the local authorities when visiting the area.

What are the top things to do in Summerland Key, FL?

Summerland Key is a beautiful island in the Florida Keys, and there are lots of exciting activities to enjoy. Here are the top four things to do in Summerland Key:

  • Go fishing in the Gulf of Mexico
  • Visit the Dolphin Research Center
  • Explore the coral reefs
  • Take a kayak tour of the mangroves

No matter what you choose to do, Summerland Key is sure to offer a memorable experience.

Where is Summerland Key, FL?

Summerland Key, FL is located in the lower Florida Keys, about 20 miles east of Key West. It is a small island community, with a population of just over 1,000 people. It is known for its beautiful beaches, fishing, and boating opportunities.

What are the popular shopping destinations in Summerland Key, FL?

Popular shopping destinations in Summerland Key, FL include:

  • The Summerland Key Cove Shopping Center
  • The Summerland Key Mini Mall
  • The Summerland Key Shopping Plaza

Is Summerland Key, FL safe to travel to?

Summerland Key, FL is generally considered safe to travel to. Here are some key safety tips to keep in mind:

  • Be aware of your surroundings and exercise caution when walking around.
  • Pay attention to local news and weather reports.
  • Be aware of the potential for natural disasters and take necessary precautions.

What is the culture like in Summerland Key, FL?

Summerland Key is an island community located off the coast of Florida near Key West. It is known for its laid-back lifestyle and friendly atmosphere.

  • The locals are welcoming and open to meeting new people.
  • The area has a relaxed atmosphere and is perfect for peaceful getaways.
  • The local cuisine features fresh seafood and tropical fruits.
  • The beaches are perfect for swimming, fishing, and sunbathing.
  • There are plenty of outdoor activities to enjoy, such as biking, kayaking, and snorkeling.

Where can I find affordable accommodation in Summerland Key, FL?

Summerland Key, FL offers a wide variety of affordable accommodations perfect for any traveler. Here are four great options:

  • Casa Cielo Resort: A luxurious and affordable option located near the beachfront with a variety of amenities available.
  • The Keys Inn: A budget-friendly hotel located just minutes away from the local attractions and activities.
  • Avalon Resort: An intimate resort with a private beach and a large selection of room types to choose from.
  • Summerland Key Vacation Homes: A variety of private vacation homes located in the heart of Summerland Key.

What are the must-visit tourist attractions in Summerland Key, FL?

Summerland Key, FL is a great destination for tourists looking to get away from it all. Here are some of the must-visit attractions in the area:

  • Bahia Honda State Park
  • Curry Hammock State Park
  • Looe Key National Marine Sanctuary
  • Cudjoe Key Visitor Center

These attractions offer a wide range of activities for visitors, from swimming and snorkeling to fishing and camping. There are also many great restaurants and bars in the area, making Summerland Key, FL a great destination for a summer getaway.

What are the most popular vacation rental amenities in Summerland Key?

  • Internet / Wifi
  • Air conditioner
  • Laundry

Explore near Summerland Key

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration

Keep exploring