
Holiday rentals with beach access in Summerland Key
Find and book unique accommodation with beach access on Airbnb
Top-rated Accommodation with Beach Access in Summerland Key
Guests agree: These holiday homes with beach access are highly rated for location, cleanliness and more.

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Beautiful Cottage & Amenities in Gated Community
Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

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.

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.

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!

Private Pool Tropical Oasis - Centrally Located
Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

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.

Waterfront Cozy Modern Retreat w/Deep Canal
Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

Exquisite Oceanfront Paradise - Key Colony Beach
Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated studio condo in Key Colony Beach, Florida Keys. Unit #10 offers one king bed, a fully equipped kitchen with full-size appliances and essentials, reliable WiFi, and a SmartTV for a comfortable stay. Enjoy the heated pool and private sandy beach just steps away. Sunset Park is next door-perfect for catching a beautiful Florida Keys sunset.

*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.

4BR 3B, Heated Pool & Spa, 60' Dock
Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)

Paradise found
Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.
Popular amenities for Summerland Key Accommodation with Beach Access
Apartment rentals with beach access

Seaside Villa~ Charming Beachfront Condo w/ Pool!

Key West ocean front Resort w/private sandy beach

Quiet Canalfront Retreat • Near Sombrero Beach

Beachside Unit 22 - Private Beach on Atlantic

Duval Balcony - Street Suite

New Waterfront Views | Pool & Tiki Bar

Rare Beach Front Resort Key West- 2BD/2BA

Henry's Penthouse On The Ocean
Holiday House Rentals with beach access

Pelican's Roost, Waterfront comfort at Venture Out

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Cozy 2 br/2 bath home in Cudjoe

Oceanfront mermaid house pool and dock

Waterfront 2-bedroom Home w/Pool and Spa

Beach Bum Bungalow #79 - Cudjoe Key, Ocean Views

Beautiful open plan remodeled home in Key Colony
Holiday condos with beach access

Villa 5027 on Duck Key BOAT SLIP available

Beachfront tropical oasis pool ocean views U33

Affordable Beachfront Luxury Condo Sleeps 6

Marathon 2BR Waterfront property on Resort

Private Beach in Marathons Key Colony Beach

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

Paradise found! Sea-Esta Condo beach and pool.

P41 - Beach Front condo with 2 bedrooms, 2 bath, p
When is the best time to visit Summerland Key?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $397 AUD | $427 AUD | $482 AUD | $362 AUD | $344 AUD | $326 AUD | $384 AUD | $341 AUD | $287 AUD | $352 AUD | $373 AUD | $415 AUD |
| 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 50 holiday rentals in Summerland Key

Nightly prices starting at
Summerland Key holiday rentals start at $111 AUD per night before taxes and fees

Verified guest reviews
Over 1,930 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Summerland Key holiday rentals include Wi-Fi 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 beach access Monroe County
- Rentals with beach access Florida
- Rentals with beach access United States
- Sombrero Beach
- Smathers Beach
- Long Beach
- Sea Oats Beach
- Bahia Honda State Park
- Conch Key
- Sunset Park
- Ernest Hemingway Home & Museum
- Fort Zachary Taylor Historic State Park
- Seven Mile Bridge
- The Turtle Hospital
- Dolphin Research Center
- Florida Keys Aquarium Encounters
- Robbies Marina Of Islamorada
- Key West Lighthouse Museum
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Boyd's Key West Campground
- Calusa Beach & Loggerhead Beach
- Boca Grande Key





