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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 serene beach scene captures soft sands meeting clear waters under a bright blue sky. Lush palm trees frame the view, while visitors are seen enjoying the tranquil coastline and gentle waves. Green foliage and distant beach cabanas are also visible, enhancing the natural beauty.
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 Tiki Hut provides shaded outdoor seating, featuring a dining table with chairs overlooking the bay. Sunning loungers are positioned nearby on a paved deck, with boats docked along the waterfront in the background, surrounded by palm trees and calm water.
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
4.87 out of 5 average rating, 15 reviews

Blue Heaven Waterfront Home

Lobstering paradise 2 houses from open water, deep 60' canal, gorgeous water views, direct access to the Atlantic/Gulf, 35' dock/seawall. 3 zone mini split A/C and heat, overhead ceiling fans, fully stocked kitchen, microwave, washer/dryer, 42" Smart TV in living room and master bedroom, WIFI. King size bed in the master, queen bed in 2nd bedroom, and a queen sofa in the living room. Beach towels, linens. Marina store with bait & fuel onsite, 2 wide boat ramps, pool, hot tub & Rec center.

Superhost
Home in Cudjoe Key
4.86 out of 5 average rating, 7 reviews

Tropical Paradise

Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.

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
The resort-style pool is surrounded by lush tropical landscaping, featuring palm trees and colorful plants. Lounge chairs are positioned near the pool's edge, reflecting in the calm water. Clear blue skies enhance the tranquil ambiance of this inviting outdoor space.
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!

Guest favorite
The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.
Boat in Islamorada
4.93 out of 5 average rating, 383 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

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
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
A serene waterfront view is captured, featuring a clear blue sky and calm waters. A wooden pier extends into the water, flanked by smooth stones along the shore. Green chairs are positioned for relaxation, nestled among lush greenery and mangroves.
Home in Summerland Key
4.95 out of 5 average rating, 108 reviews

Waterfront Anchor 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 Haven 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!

Superhost
A spacious outdoor patio is visible through large glass doors, featuring modern seating and a grill. The stunning view of the crystal-clear water and distant horizon showcases the beauty of the Florida Keys. Potted plants add a touch of greenery to the space.
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
4.93 out of 5 average rating, 46 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.

Popular amenities for Summerland Key vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Other great vacation rentals in Summerland Key

An outdoor patio area features a large table with six chairs under a shade structure. A charcoal grill is positioned nearby, with lush greenery and native plants surrounding the space. The area overlooks a tranquil mangrove landscape, enhancing the outdoor experience.
Home in Summerland Key
4.78 out of 5 average rating, 86 reviews

Kelly’s Kabin - Private FL Keys Cottage

A refreshing pool area is highlighted by a thatched-roof Tiki hut and surrounded by palm trees. Several lounge chairs are positioned near the water, while a playful basketball hoop stands at the edge of the pool. A view of the water and surrounding greenery enhances the setting.
Home in Summerland Key
4.86 out of 5 average rating, 42 reviews

Powell Family Resort

A vibrant sunset casts warm hues over the water, creating a mirror-like reflection. A wooden dock extends into the foreground, leading to the horizon, surrounded by silhouettes of trees along the shoreline. Outdoor seating is visible near the water's edge.
Home in Summerland Key
4.57 out of 5 average rating, 100 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

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

2BR Waterview | Private Pool | Balcony | Firepit

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

Starlight Serenity - Hideaway with Stunning Views

Guest favorite
A floating home is presented amid clear waters, featuring a solar panel roof. A white railing encircles the deck, which hosts outdoor seating. Green mangroves are visible in the background, and the home is anchored to the water by visible lines.
Houseboat in Islamorada
4.79 out of 5 average rating, 53 reviews

Perfect escape to the ocean

Cottage in Cudjoe Key
4.81 out of 5 average rating, 111 reviews

OCEANIA... water front cottage retreat ~

Home in Big Pine Key
4.6 out of 5 average rating, 5 reviews

Cozy house with relaxing pool

When is the best time to visit Summerland Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€255€258€274€217€211€214€223€213€186€193€212€243
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