Holiday rentals in Summerland Key
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Top-rated holiday rentals in Summerland Key
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Oceanfront Cottage with Open Water Views
Oceanview Serenity provides stunning open water views, and a 60 foot seawall for your boat. Comes with paddle board, kayaks, and more. Newly renovated 2BR cottage sleeps MAXIMUM OF FOUR (4) GUESTS, with a King in the Master BR and one Queen size bed Guest BR (both with new JW Marriott mattresses for comfort). All new appliances! Enjoy resort amenities like a pool, hot tub, tennis, and marina store. Just 30 minutes from Key West. One-time $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON
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!
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!
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***
b watervibe
Disfruta de los sonidos de la naturaleza cuando te quedes en este lugar único. Es algo diferente para disfrutar con tu pareja de un momento romántico y divertido y así relajarse y olvidarse de la vida cotidiana. Puedes disfrutar de la pesca ,de paseos en kayak ,vivir una aventura y disfrutar de otras actividades locales.Prueba de la expericiensa y ya ustedes diran.Esta casa flotante ofrece un espacio para 2 adultos. Está Esta es una experiencia de Acampada .
3 Bedroom Home - Perfect Location & Private Pool
The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street and all major attractions. This rental listing includes the second and third floors of the home, which features three bedrooms, a private swimming pool, spacious living areas inside and outside, off-street parking, and a newly renovated chef's kitchen to prepare meals. The first story of the home will be left vacant when this listing is rented.
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.
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!
*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.
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.
Blue Palms Retreat
This 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key private heated salt water swimming pool, shaded hang out area, ping pong table, corn hole game. The pier, gazebo, kayaks and kayak launch area is shared with one other home, Latitudes. You can dock your 24' boat at the pier. The water is shallow getting out to the channel with about a 2' draft.
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.
Popular amenities for Summerland Key holiday rentals
Other great holiday rentals in Summerland Key
Ocean Vue in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
Kelly’s Kabin - Private FL Keys Cottage
Key West Beach House
OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
Cudjoe Key Home with a View
Tropical Keys Retreat | Pool | Hot Tub | Cinema
Oceanside home 111, dock,kayaks,bikes,pool,fishing
When is the best time to visit Summerland Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $385 SGD | $389 SGD | $414 SGD | $327 SGD | $319 SGD | $323 SGD | $336 SGD | $322 SGD | $280 SGD | $290 SGD | $320 SGD | $367 SGD |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°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 holiday rentals in Summerland Key
Total holiday rentals
Explore 310 holiday rentals in Summerland Key
Nightly prices starting at
Summerland Key holiday rentals start at $104 SGD per night before taxes and fees
Verified guest reviews
Over 5,900 verified reviews to help you choose
Family-friendly holiday rentals
230 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 150 rentals that welcome pets
Holiday rentals with a pool
240 properties feature pools
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Wifi availability
260 of Summerland Key holiday rentals include wifi 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
- Waterfront rentals Summerland Key
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- Rentals with a patio Summerland Key
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- Smoking-friendly rentals Summerland Key
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- Southernmost Point
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