Best Vacation Homes in Summerland Key
House
10.0(32 Reviews)
2 Bedrooms
2 Baths
8 Guests
1800 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Pet Friendly
R4,913/Night
7 Nights - R34,388
House
10.0(13 Reviews)
2 Bedrooms
2 Baths
4 Guests
1300 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
R5,638/Night
7 Nights - R39,469
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
Oceanfront- Hot Tub
- Fireplace/Heating
- Ocean View
R5,668/Night
7 Nights - R39,681
Cottage
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R6,589/Night
7 Nights - R46,126
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
Private Pool- Fireplace/Heating
Pool- Balcony/Terrace
R4,872/Night
7 Nights - R34,112
House
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pool
Kitchen
Parking
R4,746/Night
7 Nights - R33,219
House
9.8(124 Reviews)
3 Bedrooms
1 Bath
5 Guests
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
R8,845/Night
7 Nights - R61,907
Cottage
9.8(60 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R4,015/Night
7 Nights - R28,104
Summerland Key Luxury Rentals
House
10.0(51 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R21,462/Night
7 Nights - R150,231
House
8.8(70 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R19,310/Night
7 Nights - R135,164
House
7 Bedrooms
6 Baths
16 Guests
- Hot Tub
- Pet Friendly
Air Conditioner
Internet
R17,834/Night
7 Nights - R124,838
House
10.0(3 Reviews)
4 Bedrooms
4 Baths
14 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R17,453/Night
7 Nights - R122,175
House
5 Bedrooms
4 Baths
14 Guests
3564 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R15,646/Night
7 Nights - R109,527
House
9.4(3 Reviews)
7 Bedrooms
4 Baths
14 Guests
- Private Pool
- Pool
- Kitchen
- Parking
R13,777/Night
7 Nights - R96,441
House
4 Bedrooms
3 Baths
8 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
R12,896/Night
7 Nights - R90,272
House
4 Bedrooms
3 Baths
6 Guests
2400 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R12,786/Night
7 Nights - R89,509
Summerland Key Pet Friendly Vacation Rentals
Cottage
9.8(50 Reviews)
1 Bedroom
1 Bath
4 Guests
480 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R4,339/Night
7 Nights - R30,377
Cottage
9.8(46 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R3,935/Night
7 Nights - R27,552
Cottage
9.8(41 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
R3,303/Night
7 Nights - R23,120
Cottage
9.4(30 Reviews)
2 Bedrooms
2 Baths
8 Guests
1500 ft²
- Pool
- Pet Friendly
- Kitchen
- Parking
R6,988/Night
7 Nights - R48,919
House
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
R7,185/Night
7 Nights - R50,299
House
2 Bedrooms
2 Baths
6 Guests
2500 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R5,181/Night
7 Nights - R36,271
House
10.0(17 Reviews)
3 Bedrooms
3 Baths
8 Guests
2237 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,830/Night
7 Nights - R26,805
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,391/Night
7 Nights - R51,744
Summerland Key Large Vacation Homes
Villa
2 Bedrooms
2 Baths
5 Guests
1053 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R10,084/Night
7 Nights - R70,594
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
2200 ft²
- Private Pool
- Pool
- Pet Friendly
- Kitchen
R8,354/Night
7 Nights - R58,482
House
10.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R8,469/Night
7 Nights - R59,277
House
9.8(9 Reviews)
5 Bedrooms
3 Baths
10 Guests
3300 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R11,337/Night
7 Nights - R79,361
House
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
8.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
1074 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
R5,889/Night
7 Nights - R41,223
House
5 Bedrooms
3 Baths
8 Guests
2500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R11,636/Night
7 Nights - R81,456
House
5 Bedrooms
6 Baths
12 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R10,249/Night
7 Nights - R71,746
House
10.0(10 Reviews)
4 Bedrooms
5 Baths
12 Guests
4000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R18,102/Night
7 Nights - R126,705
Why Choose Rent By Owner for your Summerland Key Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Summerland Key
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you can enjoy the region’s warm weather and vibrant atmosphere, making your stay in Summerland Key, Florida, USA, truly memorable and stress-free.
Peak Season Highlights
Winter (December to February)
During the winter months, you'll experience warm temperatures that make this destination a popular escape for those seeking sunshine and outdoor activities. The region's inviting climate attracts visitors looking for a relaxing getaway in cozy vacation rentals.
Average Temperature Daytime: 75°F - 80°F - Nighttime: 65°F - 70°F
Spring (March to May)
Springtime brings vibrant weather and pleasant conditions, making it an ideal period to enjoy outdoor pursuits and explore the area’s natural beauty. This season sees an increase in visitors booking vacation rentals for a memorable stay.
Average Temperature Daytime: 78°F - 82°F - Nighttime: 66°F - 70°F
Off-Season Highlights
Summer (June to August)
While summer can be popular, early or late in the season offers quieter times with fewer crowds. The warmest weather is perfect for water activities, even as prices for vacation rentals may decrease slightly.
Average Temperature Daytime: 85°F - 88°F - Nighttime: 74°F - 77°F
Fall (September to November)
Autumn presents a slower pace with mild weather and fewer tourists, making it a great time to find more affordable vacation rentals. The area's tranquil ambiance is ideal for unwinding before the winter rush.
Average Temperature Daytime: 78°F - 82°F - Nighttime: 67°F - 71°F
Weekly Weather Forecast for Summerland Key
How to Book Your Summerland Key Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Summerland Key
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for relaxing meals under the sun or stars.
- Take advantage of private patios or decks that offer stunning views of the surrounding waters.
- Make use of well-maintained swimming pools to cool off on warm summer days in this tropical destination.
- Explore lush gardens or landscaped yards that provide a peaceful setting for outdoor leisure.
- Utilize direct access to beaches or waterfronts, ideal for boating, fishing, or simply unwinding by the water.
- Benefit from covered outdoor spaces designed for comfort during breezy evenings or rainy days.
- Leverage outdoor grills or barbecue setups to enjoy cookouts and social gatherings here in the region.
Top Attractions Around Summerland Key
What attractions are nearby?
In this charming destination, you can explore a variety of outdoor activities such as boating, fishing, and snorkeling just moments from your vacation rental, allowing you to fully enjoy the natural beauty and aquatic adventures that make the area so popular among visitors.
Family Activities
- Snorkeling Adventures: Discover the vibrant marine life just off the shores, making it a perfect family activity to explore the clear waters surrounding Summerland Key.
- Wildlife Watching at Local Parks: Enjoy observing native birds and aquatic creatures in the region’s parks, offering an educational and entertaining experience for all ages.
- Kayaking Excursions: Paddle through calm, scenic waterways that provide a fun way for families to immerse themselves in the natural beauty of this destination.
- Beach Day Outings: Relax on pristine beaches where you can build sandcastles, swim, or simply soak up the sun with loved ones in this idyllic coastal area.
Adult Activities
- Snorkeling and Diving: Explore the vibrant coral reefs and marine life just off the coast, making it a perfect activity to experience here in this tropical region.
- Fishing Expeditions: Join local charters for a deep-sea fishing adventure that offers the chance to catch a variety of sportfish in the area’s abundant waters.
- Boat Tours and Water Activities: Discover scenic waterways and enjoy paddleboarding or kayaking, providing tranquil moments surrounded by natural beauty.
- Sunset Cruises: Relax on a sunset cruise to take in stunning views over the Gulf, offering a memorable way to unwind and appreciate the area's breathtaking scenery.
Other Places to Stay in Summerland Key, FL
MiLo Watersports
Reel Deal Fishing Charters
Melody Key
Summerland Key Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Water Activities: Make the most of your stay by engaging in water-based activities such as kayaking or paddleboarding to enjoy the region's scenic coastlines and clear waters.
- Visit Early or Off-Peak: Maximize your experience by visiting popular spots during early mornings or off-peak hours when the area is less crowded and more peaceful.
- Discover Hidden Gems: Take time to explore lesser-known beaches and local eateries to get an authentic taste of what the destination truly offers.
- Plan Your Trip Around the Weather: Check the regional weather forecast to plan outdoor adventures on days with ideal conditions, ensuring a comfortable and enjoyable stay here.
Transportation Options
- Rental Cars: You can easily rent a vehicle in the area to explore Summerland Key and its surrounding sights at your own pace.
- Public Transportation: Local bus services provide an affordable way to navigate here without the need for a car.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options are readily available for convenient, door-to-door transportation within the region.
- Bicycle Rentals: Biking is a popular choice for exploring the scenic views of the area while enjoying a healthy, eco-friendly mode of travel.
Local Customs Options
- Reef Snorkeling Etiquette: You’ll find that respecting the vibrant coral reefs and marine life is a key custom here, ensuring your snorkeling adventures are environmentally responsible and enjoyable.
- Local Seafood Dining Traditions: Embracing the area's seafood cuisine, you are encouraged to sample the fresh catch of the day while observing proper dining etiquette rooted in coastal traditions.
- Eco-Friendly Practices: Visitors often participate in sustainable practices such as recycling and conserving water, reflecting the community’s commitment to preserving this delicate coastal environment.
- Respect for Marine Conservation Laws: It’s customary to follow all local regulations on fishing and wildlife interaction to protect the region’s unique ecosystems and enjoy your stay responsibly.
Frequently Asked Questions About Summerland Key?
1. What are the top vacation rentals in Summerland Key?
There are a lot of options in Summerland Key. If you plan on staying in the Summerland Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Summerland Key:
- Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
- Canal Front (Deep Water) Tropical Villa
- Ground Level Home With Deepwater Canal
- Ocean Front Modern Home
- Oceanfront Sunsets in the Florida Keys
- LIVING IN BEAUTIFUL PARADISE
- Views Views! Direct Oceanfront, Beautiful Inside!
- Summer Month's Just Opened Up! Canal Front Pool Home in Summerland Key
- Fishermens' dream B.Y.O. boat ocean front with protected canal 600' to bluewater
- Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
2. How many vacation rentals have private pools in Summerland Key?
There are 30 vacation rentals with private pools near Summerland Key. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Summerland Key are best for families?
If you are looking for a family-friendly vacation home in Summerland Key, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Summerland Key:
4. How many Rentbyowner vacation rentals are available in Summerland Key?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 115 in the Summerland Key area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Summerland Key.
5. What is the cancellation policy for bookings in this area?
Cancellation policies vary by property, so it's important to review the specific listing details. You can find the policy outlined on the property page or contact the owner directly for clarification.
6. Are there any additional fees I should expect when booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes are often detailed in the listing. Make sure to read the fee breakdown before confirming your reservation to avoid surprises.
7. How do I confirm my reservation and what is required at check-in?
Reservation confirmation typically involves completing the booking through the listing platform and receiving a confirmation email. Check-in instructions, including key collection or access codes, are provided by the host prior to your arrival.
8. Is there a minimum stay requirement during peak seasons?
Minimum stay requirements can differ depending on the time of year and property policies. Details about any stay restrictions are usually listed on the property page or can be confirmed by contacting the owner directly.
9. What amenities are available in vacation rentals in this region?
Most rentals offer a range of amenities like Wi-Fi, air conditioning, kitchens, and waterfront views. For specifics, refer to the property description or reach out to the owner to ensure it meets your needs.
Summerland Key Top Rated Vacation Rentals
House
10.0(18 Reviews)
4 Bedrooms
3 Baths
9 Guests
2768 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R8,306/Night
7 Nights - R58,141
House
10.0(17 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R7,678/Night
7 Nights - R53,741
House
10.0(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
2070 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R5,773/Night
7 Nights - R40,411
House
10.0(9 Reviews)
4 Bedrooms
3 Baths
8 Guests
1900 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R9,409/Night
7 Nights - R65,869
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1300 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R4,692/Night
7 Nights - R32,845
New
House
10.0(3 Reviews)
2 Bedrooms
4 Baths
6 Guests
1292 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R5,234/Night
7 Nights - R36,644
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
R4,450/Night
7 Nights - R31,140
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R6,802/Night
7 Nights - R47,620
