We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

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.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Cottage in Cudjoe Key

4.9 out of 5 average rating, 134 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!

Dec 12 – 19

ﺩ.ﺇ3,195 per night

Home in Key West

4.94 out of 5 average rating, 272 reviews

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.

Oct 3 – 10

ﺩ.ﺇ1,867 per night

Home in Cudjoe Key

4.81 out of 5 average rating, 124 reviews

Ocean View 2/2 on Canal

Hurricane Ian did no damage This is a non-smoking, no pets, canal front home with a 35' sea wall. Ocean views from either deck. Vaulted great room. Fully equipped kitchen and linens with two private bed/bath suites offering privacy. The resort is gated and secure with plenty of amenities: a small tiki beach, marina, large pool, hot tub, pickle ball, tennis,laundry and general store. One time $113.00 resort fee Required to book: 1. verified identity 2. have positive reviews on AIrbnb

Jul 29 – Aug 5

ﺩ.ﺇ1,474 per night

Guest suite in Marathon

4.98 out of 5 average rating, 186 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Jul 7 – 14

ﺩ.ﺇ798 per night

Home in Cudjoe Key

4.9 out of 5 average rating, 104 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Oct 30 – Nov 6

ﺩ.ﺇ1,467 per night

Boat in Islamorada

4.92 out of 5 average rating, 327 reviews

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.

Nov 26 – Dec 3

ﺩ.ﺇ686 per night

Condo in Key Colony Beach

4.91 out of 5 average rating, 197 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Jan 1 – 8

ﺩ.ﺇ1,996 per night

Guesthouse in Key West

4.93 out of 5 average rating, 528 reviews

Old Town - Room Opens to Pool and Garden

Located in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Jun 22 – 29

ﺩ.ﺇ1,240 per night

Home in Marathon

4.9 out of 5 average rating, 136 reviews

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.

Feb 8 – 15

ﺩ.ﺇ1,208 per night

Camper/RV in Big Pine Key

4.93 out of 5 average rating, 41 reviews

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.

Jul 16 – 23

ﺩ.ﺇ443 per night

Home in Cudjoe Key

4.89 out of 5 average rating, 193 reviews

Newly Renovated Oceanside House with Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

Apr 1 – 8

ﺩ.ﺇ1,493 per night

Houseboat in Key West

4.91 out of 5 average rating, 193 reviews

Key West Luxury Houseboat

EXPANSIVE OCEAN VIEW. 2 Queen Bdrms with Large Ensuite Baths on 1st level. Ocean view 2nd Level Living Room and Full Kitchen with half bath. Spacious fore and aft decks. 15 min from downtown KEY WEST. Located at Stock Island Yacht Club. Panoramic Views from 3rd level sun deck POOL, PRIVATE BEACH, Gym.

Apr 3 – 10

ﺩ.ﺇ2,462 per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Summerland Key beach access rentals

Free parking on premises

Air conditioning

Apartment rentals with beach access

Apartment in Key West

4.84 out of 5 average rating, 693 reviews

Duval Balcony - Street Suite

Oct 4 – 11

ﺩ.ﺇ1,237 per night

Apartment in Key West

4.92 out of 5 average rating, 175 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

Dec 11 – 18

ﺩ.ﺇ2,363 per night

Apartment in Key West

4.89 out of 5 average rating, 136 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Oct 6 – 13

ﺩ.ﺇ2,010 per night

Apartment in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

Oct 10 – 17

ﺩ.ﺇ1,038 per night

Apartment in Key Largo

4.78 out of 5 average rating, 137 reviews

Escape to the Seaside!

ﺩ.ﺇ1,180 per night

Apartment in Tavernier

5.0 out of 5 average rating, 15 reviews

Beautiful condo with a balcony

Jul 28 – Aug 4

ﺩ.ﺇ641 per night

Apartment in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

Sep 11 – 18

ﺩ.ﺇ2,555 per night

Apartment in Key Colony Beach

4.84 out of 5 average rating, 79 reviews

Beachside Unit 22 - Private Beach on Atlantic

Dec 10 – 17

ﺩ.ﺇ854 per night

House rentals with beach access

Home in Key Colony Beach

4.96 out of 5 average rating, 136 reviews

Beautiful open plan remodeled home in Key Colony

Nov 9 – 16

ﺩ.ﺇ851 per night

Home in Cudjoe Key

4.87 out of 5 average rating, 45 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Dec 1 – 8

ﺩ.ﺇ2,735 per night

Home in Key Colony Beach

5.0 out of 5 average rating, 15 reviews

Coral House: 2/2 Waterfront in KCB w/ King Beds

May 11 – 18

ﺩ.ﺇ560 per night

Home in Cudjoe Key

4.89 out of 5 average rating, 28 reviews

Cozy 2 br/2 bath home in Cudjoe

Sep 24 – Oct 1

ﺩ.ﺇ1,100 per night

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Mar 29 – Apr 5

ﺩ.ﺇ2,215 per night

Home in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Latitudes-Ocean Front Pool

Nov 9 – 16

ﺩ.ﺇ2,525 per night

Home in Marathon

5.0 out of 5 average rating, 17 reviews

Horizon

Apr 5 – 12

ﺩ.ﺇ3,786 per night

Home in Cudjoe Key

4.88 out of 5 average rating, 17 reviews

Pelican's Roost, Waterfront comfort at Venture Out

May 6 – 13

ﺩ.ﺇ1,187 per night

Condo rentals with beach access

Condo in Marathon

4.87 out of 5 average rating, 192 reviews

Sombrero Beach Tropical Getaway

Nov 10 – 17

ﺩ.ﺇ834 per night

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Sep 25 – Oct 2

ﺩ.ﺇ962 per night

Condo in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

Jan 28 – Feb 4

ﺩ.ﺇ1,934 per night

Condo in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

Oct 3 – 10

ﺩ.ﺇ1,312 per night

Condo in Tavernier

4.88 out of 5 average rating, 229 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Sep 26 – Oct 3

ﺩ.ﺇ896 per night

Condo in Key West

4.83 out of 5 average rating, 243 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

Feb 12 – 19

ﺩ.ﺇ1,854 per night

Condo in Tavernier

4.93 out of 5 average rating, 108 reviews

Keys Life Ocean Pointe Pool Jacuzzi Beach Crib

Oct 23 – 30

ﺩ.ﺇ950 per night

Condo in Tavernier

4.87 out of 5 average rating, 126 reviews

Reel Large END Unit in Ocean Point Suites

Oct 7 – 14

ﺩ.ﺇ1,093 per night

Quick stats about vacation rentals with beach access in Summerland Key

Total rentals
40 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
930 reviews
Nightly prices starting at
ﺩ.ﺇ514 before taxes and fees

Destinations to explore