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Vacation rentals in Summerland Key

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Quick stats about vacation rentals in Summerland Key

  • Total vacation rentals

    Explore 330 vacation rentals in Summerland Key

  • Nightly prices starting at

    Summerland Key vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

  • Verified guest reviews

    Over 6,470 verified reviews to help you choose

  • Family-friendly vacation rentals

    240 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 160 rentals that welcome pets

  • Vacation rentals with a pool

    260 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    280 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

  • 4.8 Average rating

    Summerland Key stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Summerland Key

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

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Guest favorite
An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.
Cottage in Cudjoe Key
4.89 out of 5 average rating, 175 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

Superhost
Tiny home in Summerland Key
4.92 out of 5 average rating, 66 reviews

Cottage

Experience island living at Sugarloaf RV Resort & Cottages in the Lower Keys, just 25 minutes from Key West. Our NEW Two-Bedroom Cottages sleep up to 6 guests with two queen beds and a full-size pull-out sofa. Enjoy a kitchenette with a double-burner stovetop, pots, pans, dorm fridge, microwave, K-Cup coffee maker, toaster, dishes, and utensils. Relax on your private patio and enjoy resort amenities including a heated / chilled pool, kayaks, paddle boards, bicycles, and a peaceful private lake.

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
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, 33 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!

Top guest favorite
Home in Summerland Key
4.97 out of 5 average rating, 30 reviews

Starlight Serenity - Hideaway with Stunning Views

Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!

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, 201 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

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
4.83 out of 5 average rating, 111 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 scenic waterfront area is depicted with vibrant green lounge chairs positioned on a sandy peninsula. Surrounding waters provide a tranquil blue hue. Wooden docks extend into the bay, complemented by lush palm trees and colorful buildings in the background.
Home in Summerland Key
4.95 out of 5 average rating, 114 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 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
4.87 out of 5 average rating, 132 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.

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.

Guest favorite
The Tiki Suite is presented on a wooden platform, showcasing thatched roofing and an inviting porch area. Two stand-up paddleboards are placed alongside the structure, with calm waters reflecting the clear sky.
Houseboat in Key West
4.91 out of 5 average rating, 554 reviews

Tiki Suites ~ Original Tiki ~ Private Water Stay

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

Superhost
Boat in Key West
5 out of 5 average rating, 4 reviews

Wake Up On The Water | Luxury Marina | Key West

Wake up to the rhythm of the water and experience Key West from a completely different perspective. Stay aboard a 45-ft sailing yacht at the Perry Hotel & Marina. Enjoy 2 pools, gym, fine dining, and a free shuttle to Old Town. Ideal for couples or close knit groups: intimate, memorable, and all part of the yacht lifestyle.

Popular amenities for Summerland Key vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Other great vacation rentals in Summerland Key

Guest favorite
A serene sunset casts warm orange and golden hues over the water, creating a calming reflection. The houseboat is visible with a cozy chair positioned towards the horizon. The surrounding calm waters and boats in the distance emphasize the peaceful setting.
Boat in Key West
4.95 out of 5 average rating, 88 reviews

*August/September specials* off Grid Boat Key West

Guest favorite
Cottage in Cudjoe Key
5 out of 5 average rating, 5 reviews

FL Keys Retreat - Community pool and hot tub

An aerial view of the cottage surrounded by lush greenery and the calm waters of a mangrove area. The property features a spacious driveway leading to the home, with natural landscapes extending towards the Gulf of Mexico in the background.
Home in Summerland Key
4.79 out of 5 average rating, 89 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

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
4.58 out of 5 average rating, 102 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Top guest favorite
A charming waterfront villa is framed by lush palm trees, featuring a spacious sandy area with vibrant landscaping. A boat is docked nearby, with soft clouds drifting across the blue sky, contributing to a serene outdoor environment.
Home in Cudjoe Key
4.96 out of 5 average rating, 27 reviews

Aug. Discount, Waterfront Retreat/Pool/golf cart

Top guest favorite
A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.
Houseboat in Marathon
4.92 out of 5 average rating, 86 reviews

b watervibe

Home in Cudjoe Key
5 out of 5 average rating, 3 reviews

Ocean Breeze Retreat w/ Dock| Keys Escape

When is the best time to visit Summerland Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,091ﺩ.ﺇ 1,102ﺩ.ﺇ 1,172ﺩ.ﺇ 925ﺩ.ﺇ 903ﺩ.ﺇ 914ﺩ.ﺇ 951ﺩ.ﺇ 911ﺩ.ﺇ 793ﺩ.ﺇ 823ﺩ.ﺇ 907ﺩ.ﺇ 1,039
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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
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