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Vacation rentals in Summerland Key

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Top-rated vacation rentals in Summerland Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost
A coastal scene showcases palm trees swaying gently by the water. Thatched roofs provide shaded seating areas along the shoreline. Sailboats are visible on the horizon, amidst clear turquoise waters under a bright blue sky, with a few fluffy clouds drifting by.
Tiny home in Big Pine Key
4.87 out of 5 average rating, 115 reviews

Cottage 30 min from Key West, free parking, pool

Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

Top guest favorite
A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.
Home in Key Colony Beach
4.93 out of 5 average rating, 137 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Guest favorite
Home in Cudjoe Key
4.95 out of 5 average rating, 86 reviews

Ocean~View w/ Dock, Pool, Kayaks, King Bed

Experience waterfront luxury in Venture Out on peaceful Cudjoe Key! Enjoy stunning Atlantic Ocean views, amazing sunsets, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Keep your boat at the house and reach the Atlantic or Gulf in minutes. Near Key West, this updated Keys getaway includes resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, especially lobster season in August, so book now!

Guest favorite
An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.
Condo in Summerland Key
4.97 out of 5 average rating, 30 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Superhost
An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.
Home in Cudjoe Key
4.84 out of 5 average rating, 121 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Guest favorite
A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.
Home in Cudjoe Key
4.82 out of 5 average rating, 106 reviews

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

Guest favorite
Aerial view of a waterfront property featuring a semi-circle dock leading to a small island. Brightly colored chairs in green and turquoise sit on sandy areas, surrounded by clear blue water and lush tropical vegetation. Nearby, additional properties can be seen amidst palm trees.
Home in Summerland Key
4.92 out of 5 average rating, 118 reviews

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Top guest favorite
A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.
Home in Cudjoe Key
4.99 out of 5 average rating, 70 reviews

Waterfront, Dock, Pool, Pickleball, near Key West!

Welcome to “The Barnacle” your waterfront home in the Florida Keys! Dock your boat behind this charming two bedroom home with 35’ sea wall! We have direct access to some of the best fishing, snorkeling and diving in the Keys! Beautiful neighborhood loaded with amenities. Bring a pole and fish from the dock! Relax, enjoy and have a wonderful vacation experience. Visit YouTube “The Barnacle at Venture Out”. Swim, Fish, Dive …Repeat!

Superhost
A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.
Home in Cudjoe Key
4.88 out of 5 average rating, 131 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Superhost
Tiny home in Summerland Key
4.94 out of 5 average rating, 47 reviews

Cottage

Experience island living at Sugarloaf RV Resort's NEW Cottages in the Lower Keys, just 25 minutes from Key West. These Two-Bedroom Cottages sleep up to 4 guests with 2 Queen beds. Features include a kitchenette with double burner stovetop, dorm fridge, microwave, single serve coffee maker, toaster, plus outdoor seating. Coastal charm with keys-style design and a private patio perfect for morning coffee or sunset relaxation.

Top guest favorite
Home in Marathon
4.95 out of 5 average rating, 200 reviews

Spacious 3Br/3Ba, 70ft Dock, Beach VACA23-16

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

Guest favorite
A serene outdoor space features palm trees swaying gently by the water's edge, with a small floating dock visible. Loungers are arranged by the pool, surrounded by pebbled landscaping and lush greenery, all under a clear blue sky.
Home in Cudjoe Key
4.9 out of 5 average rating, 39 reviews

White House - Receive $400 towards a Boat Rental!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our homes staying between the dates of Sept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026 Please reach out before booking for boat availability. Kayaks come with the rental. Small floating dock for your boat.

Popular amenities for Summerland Key vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Other great vacation rentals in Summerland Key

The cottage is depicted from above, surrounded by lush greenery and manicured landscaping. A gravel driveway leads to the property, with tropical plants lining the path. In the background, a serene mangrove area is visible, merging into the blue expanse of the Gulf of Mexico.
Home in Summerland Key
4.78 out of 5 average rating, 86 reviews

Kelly’s Kabin - Private FL Keys Cottage

A serene sunset view is captured from a wooden dock extending over calm waters. Silhouetted figures can be seen seated at the end of the dock, with vibrant orange and purple hues reflecting off the surface. Framed by natural foliage, the scene offers a peaceful atmosphere.
Home in Summerland Key
4.86 out of 5 average rating, 42 reviews

Powell Family Resort

Guest favorite
Home in Marathon
5 out of 5 average rating, 6 reviews

Beach House in Marathon with Amazing Backyard!

Home in Summerland Key
4.5 out of 5 average rating, 10 reviews

2BR Waterview | Private Pool | Balcony | Firepit

Guest favorite
An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.
Home in Cudjoe Key
4.97 out of 5 average rating, 197 reviews

Cudjoe Key Home with a View

Guest favorite
Home in Cudjoe Key
4.92 out of 5 average rating, 197 reviews

106- Newly Renovated House with Oceanview and Pool

Top guest favorite
Home in Summerland Key
4.96 out of 5 average rating, 25 reviews

Starlight Serenity - Hideaway with Stunning Views

Guest favorite
Home in Summerland Key
5 out of 5 average rating, 14 reviews

Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean

When is the best time to visit Summerland Key?

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Avg. price€256€258€275€217€212€214€223€214€186€193€213€244
Avg. temp21°C22°C24°C25°C27°C29°C30°C30°C29°C27°C25°C23°C

Frequently Asked Questions

  • What are the best places to stay in Summerland Key?

    Waterfront neighborhoods around Summerland Key have a range of vacation rentals, from homes with docks to cozy cottages. Many areas provide access to kayaking, swimming, and fishing right from your doorstep.

  • What are the best things to do in Summerland Key with kids?

    Families frequently enjoy kayaking in calm waters, visiting local marine centers, or searching for wildlife along boardwalks and beaches. Picnics by the shore and easy paddleboarding outings are often suggested for all ages.

  • What are some of the best things to do in Summerland Key?

    Guests can explore beautiful waters by kayak or paddleboard, discover coral reefs on snorkeling outings, or connect with the area's ecological side at local refuges. Fishing, birdwatching, and bicycling are also frequently suggested activities.

  • How is the weather in Summerland Key?

    Summerland Key has warm, tropical weather year-round, with temperatures ranging from about 65–91°F (19–33°C). Rain is more common in late summer and early fall, while winters tend to be drier and pleasantly mild.

  • When is the best time to visit Summerland Key?

    Milder weather and lower rainfall make late fall through early spring often recommended for visiting Summerland Key. The winter period brings comfortable temperatures and plenty of outdoor activities.

  • What are the best places to visit in Summerland Key?

    Frequently suggested spots include local marinas, waterfront parks, and tranquil canals perfect for exploring by kayak. Around the island, visitors seek out small art galleries, marine centers, and vibrant coral viewing areas.

  • What are some hiking trails in Summerland Key?

    Summerland Key has scenic walking and cycling paths along its quiet neighborhoods and waterfront areas. Nature enthusiasts often explore nearby wildlife refuges or coastal preserves for gentle trails surrounded by local flora and birdlife.

  • What are some family activities we can do in Summerland Key?

    Families often enjoy paddleboarding, gentle kayaking, or discovering coastal boardwalks. Picnic spots by the water and exploring marine-themed attractions provide engaging experiences for all ages.

  • What are some of the best day trip ideas from Summerland Key?

    Popular day trips include exploring neighboring islands for snorkeling, unique marine centers, and art galleries. Visitors also venture around to discover historic sites, state parks, and environmental centers focused on the Keys' natural setting.

  • Are there any pet friendly accommodations available in Summerland Key?

    Summerland Key has pet-friendly accommodations, including vacation rentals with outdoor spaces for pets and access to walkable, quiet neighborhoods. Many hosts welcome travelers with dogs or cats, making it easy to enjoy the area together.

  • What are some local tips for visiting Summerland Key?

    Locals often suggest bringing extra sun protection and water gear to make the most of shoreline activities. Early mornings and evenings can be quieter for wildlife watching, while exploring local eateries gives a sense of the community’s flavors.

  • What is Summerland Key known for?

    Summerland Key is known for its laid-back atmosphere, easy ocean access, and strong ties to marine culture. The area attracts those interested in boating, diving, and observing coastal wildlife in a relaxed community setting.

  • What are the best hidden gems to explore in Summerland Key?

    Travelers sometimes seek out quiet canals, small community parks, or lesser-known snorkeling spots around the island. Local art studios and family-run seafood eateries also reflect Summerland Key's character outside the usual path.

  • What are the best foods to try in Summerland Key?

    Local menus frequently feature fresh seafood like lobster, conch fritters, and fish sandwiches, along with tropical fruit desserts and traditional Key lime pie. Small eateries and bar-grills provide a taste of island-style cooking.

  • What should I bring for a trip to Summerland Key?

    Pack lightweight, sun-protective clothing, a wide-brimmed hat, and sturdy sandals or water shoes. Reusable water bottles, reef-safe sunscreen, and swim gear help make the most of outdoor adventures.

  • What is the nightlife in Summerland Key like?

    Nightlife on Summerland Key is relaxed, focused on casual waterfront bars, live music evenings, and outdoor dining. The scene highlights local musicians and a laid-back island atmosphere rather than large clubs.

  • What are the most popular events or festivals in Summerland Key?

    Seasonal community celebrations, boating tournaments, and Keys-style arts festivals are frequently highlighted by locals. The area also participates in regional festivities tied to island culture, fishing, and marine life throughout the year.

  • Are there family friendly vacation rentals in Summerland Key?

    Summerland Key has a variety of family-friendly vacation rentals, including homes with kitchens, waterfront access, and outdoor gathering spaces. Many options are designed to accommodate groups and children comfortably.

Quick stats about vacation rentals in Summerland Key

  • Total vacation rentals

    Explore 310 vacation rentals in Summerland Key

  • Nightly prices starting at

    Summerland Key vacation rentals start at €69 per night before taxes and fees

  • Verified guest reviews

    Over 5,900 verified reviews to help you choose

  • Family-friendly vacation rentals

    230 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Vacation rentals with a pool

    240 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    260 of Summerland Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Summerland Key rentals

  • 4.7 Average rating

    Summerland Key stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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  4. Monroe County
  5. Summerland Key