
Holiday rentals with beach access in Summerland Key
Find and book unique rentals with beach access on Airbnb
Top-rated rentals with beach access in Summerland Key
Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

Key Colony Beach Luxury Condo, New Modern Interior
Private studio condo at Key Colony Beach with a private balcony, heated pool and sandy beach. Unit #15 was recently renovated and offers one comfy King size bed and a fully equipped kitchen with essentials (stove, oven, toaster, microwave, blender, fridge, cooking utensils). Wifi, Amazon Echo and a TV. Enjoy a short walk to Sunset Park next door to experience a stunning Florida Keys sunset. Guests also have access to a private beach with lounge chairs, patio tabales, tiki huts, and BBQ grills.

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

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.

Waterfront Sanctuary in the Keys!
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Hidden Beach unit 1 The Perfect Place to stay
This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

Beachside Unit 37 - Come Relax on the Atlantic!
Unit 37 Details: Second Floor, Walk-in shower, Two Queen Beds, Twin Sofa Sleeper, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.” Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean.

Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Paradise in Key Colony Beach + Cabana Club
Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

*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.

Having fun in the lower Keys
Enjoy the lovely setting of this romantic spot in nature. Big Pine Key is in the center of the lower Keys just 35 miles from Key West making it convenient to all the tourism and night life adventure the Keys have to offer while simultaneously being far enough away to allow for an off the beaten path relaxing experience. I have left several destinations for diving , fishing and/or great spots to just relax and take in the sun.

Beachfront Condo w/ Ocean Views in Marathon
Beautifully decorated 2nd floor end unit with stunning panoramic ocean views from the balcony, living room and master bedroom. Two bedrooms / two full bathrooms and washer and drier in unit. Full kitchen. Directly on the beach! Beach chairs, umbrellas and towels provided for you. Guests have access to the heated swimming pool, tennis court and beach. Master bedroom king-size memory foam mattress

KCB Waterfront Split Home Walkable to Cabana Club
3BR/ 2 BA stilt home on crystal clear canal with open water views on deep water with 30 foot boat slip on a cul de sac. Short walking distance to multiple restaurants/bars, shops, and the Cabana Club with beach, pool, and hot tub. Fenced in waterfront patio with tiki hut. Kid friendly, with toys and high chair. Covered parking. Guests required to sign Regulations for Key Colony Beach form.
Popular amenities for rentals with beach access in Summerland Key
Apartment rentals with beach access

Seaside Villa~ Charming Beachfront Condo w/ Pool!

Key West Beachside 1400sf, 2 Bedroom Condo

Duval Balcony - Street Suite

#1 Island Hideaway 89 - OCEAN FRONT

Marathon Studio on Lovely Gulf Front Resort

Dock POOL Kayaks Bikes Beach2mi WalkToStores

Luxury Waterfront Suite w/ Marina, Pool, Tiki Bar

2 Bdrm Oceanfront Complex Private Beach & Pool
House rentals with beach access

Florida Keys Oceanside Utopia

Pelican's Roost, Waterfront comfort at Venture Out

Dock, Beach Club, Ocean & Gulf Access, Pickle Ball

KCB Tropical Escape

Ultra Quiet & Peaceful Getaway Marathon Treehouse

Waterfront Oasis w/Private Pool-Dockage-Beach

Waterfront House with 37 ft Dock & Cabana Club

Golf Coast Oasis near Sombrero Beach
Apartment rentals with beach access

"O" Fish Ally Paradise @Ocean Isle Fishing Village

Ocean Front Studio private Sandy Beach in Key West

Villa 5087 on Duck Key BOAT SLIP available

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Affordable Beachfront Luxury Condo Sleeps 6

Private Beach in Marathons Key Colony Beach

Fully renovated 2/2 bath condo w/ shared pool!

Paradise found! Sea-Esta Condo beach and pool.
When is the best time to visit Summerland Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £214 | £241 | £217 | £189 | £180 | £171 | £201 | £179 | £150 | £188 | £199 | £216 |
| 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 |
Quick stats about holiday rentals with beach access in Summerland Key

Total holiday rentals
Explore 60 holiday rentals in Summerland Key

Nightly prices starting at
Summerland Key holiday rentals start at £65 per night before taxes and fees

Verified guest reviews
Over 1,910 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
60 of Summerland Key holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Summerland Key rentals

4.8 Average rating
Summerland Key stays are highly rated by guests – averaging 4.8 out of 5!
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- Rentals with a kayak Summerland Key
- Rentals with beach access Monroe County
- Rentals with beach access Florida
- Rentals with beach access United States
- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- Sea Oats Beach
- Conch Key
- Bahia Honda State Park
- Long Beach
- Florida Keys Aquarium Encounters
- Sunset Park
- Southernmost Point
- Seven Mile Bridge
- Key West Butterfly & Nature Conservatory
- Dolphin Research Center
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Key West Lighthouse Museum
- Robbies Marina Of Islamorada
- The Turtle Hospital
- Boyd's Key West Campground




