
Vacation rentals with beach access in Summerland Key
Find and book unique beach access rentals on Airbnb
Top-rated beach access rentals in Summerland Key
Guests agree: these beach access rentals 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!

Hidden Beach Duplex, Best Place in Key West
Go to sleep and wake up smiling listening to the waves. 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. This is an extraordinary condo on an extraordinary property. This is nicest unit of 3 for rent at Hidden Beach. If you are discerning, this really is best place place to stay in Key West.

Poolside Cottage #411
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

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.

*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.

Coco Plum Waterfront Hideaway Home in Marathon
This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

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.

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV
See our home on HGTV's "Vacation House for Free", (Rental Lisc#VACA-20-690) BRING YOUR BOAT TO OUR PRIVATE 60 FOOT DOCK WITH 30 AMP SHORE POWER OUTLET. We call our home "Bahama Breeze" because that's what you feel blowing in as you spend your vacation at this Oceanside single family home.
Popular amenities for Summerland Key beach access rentals
Apartment rentals with beach access

Key West Beachside 1400sf, 2 Bedroom Condo

Beachside Unit 22 - Private Beach on Atlantic

Duval Balcony - Street Suite

New! Waterfront Views | Pool & Tiki Bar

Henry's Penthouse On The Ocean

Dock POOL Kayaks Bikes Beach2mi WalkToStores

2 Bdrm Oceanfront Complex Private Beach & Pool

Oceanview condo w/pool, jacuzzi
House rentals with beach access

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

Cozy 2 br/2 bath home in Cudjoe

Tropical Island Getaway

Waterfront home w/pool, dock & close to beach

Paradise Ocean Front 4/3Home Heated Pool

Viamarhe House-Private beach, Kayak, yard games

Waterview from three sides, Cabana Club, 30' Docks

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor
Condo rentals with beach access

Ocean front 1BR/1BA Suite w/ kitchen & living rm

Affordable Beachfront Luxury Condo Sleeps 6

*NEW*May the Surf Be With You-Florida Keys Retreat

Private Beach in Marathons Key Colony Beach

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

Paradise found! Sea-Esta Condo beach and pool.

Coastal Key Colony Beach Condo, Oceanfront Complex

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 | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$61,830 GYD | G$69,559 GYD | G$62,666 GYD | G$54,728 GYD | G$52,012 GYD | G$49,297 GYD | G$58,070 GYD | G$51,595 GYD | G$43,448 GYD | G$53,266 GYD | G$56,399 GYD | G$62,666 GYD |
| 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 vacation rentals with beach access in Summerland Key

Total vacation rentals
Explore 60 vacation rentals in Summerland Key

Nightly prices starting at
Summerland Key vacation rentals start at G$18,800 GYD per night before taxes and fees

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

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Summerland Key vacation 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
- Calusa Beach & Loggerhead Beach
- Long Beach
- Sea Oats Beach
- Bahia Honda State Park
- Conch Key
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Sunset Park
- Dolphin Research Center
- Robbies Marina Of Islamorada
- Key West Lighthouse Museum
- Florida Keys Aquarium Encounters
- Key West Butterfly & Nature Conservatory
- The Turtle Hospital
- Boyd's Key West Campground
- Southernmost Point




