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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.

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Cottage in Cudjoe Key

4.91 out of 5 average rating, 133 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!

3–10 Mar

₹74,050 per night

Guest favourite

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.

2–9 Apr

₹48,119 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

19–26 Aug

₹34,176 per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 185 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.

12–19 Oct

₹18,496 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.

17–24 Jan

₹33,980 per night

Guest favourite

Home in Key Largo

4.98 out of 5 average rating, 119 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

23–30 Aug

₹17,228 per night

Cottage in Islamorada

4.81 out of 5 average rating, 143 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

5–12 Sep

₹14,801 per night

Houseboat in Key West

4.84 out of 5 average rating, 176 reviews

Happys Houseboat

This beautiful houseboat is nestled in a calm protected bay, it has hot water, a fridge and Air Conditioning! This boat was featured in Old Dominion‘s music video “I was on a boat that day”. Beautiful sites all around to wake up on the water and sunsets and stars to experiences as you relax on the top deck in the evening. Included in the rental is use of a skiff to get to and from land and and a seventh generation local captain to assist in check in and give a tour of the Houseboat.

26 May – 2 Jun

₹33,724 per night

Guest favourite

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.

8–15 Apr

₹15,923 per night

Guest favourite

Guest house in Key West

4.93 out of 5 average rating, 527 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.

22–29 Jun

₹28,728 per night

Guest favourite

Apartment 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.

29 Oct – 5 Nov

₹29,078 per night

Guest favourite

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise at Cudjoe Bay

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

15–22 Jan

₹34,469 per night

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Popular amenities for rentals with beach access in Summerland Key

Free parking on premises

Air conditioning

Apartment rentals with beach access

Flat in Key West

4.84 out of 5 average rating, 692 reviews

Duval Balcony - Street Suite

17–24 Jul

₹28,652 per night

Guest favourite

Flat in Key Largo

4.98 out of 5 average rating, 125 reviews

Key Largo Kawama Lagoon Free Cancel Deutsch Spain

29 Jul – 5 Aug

₹26,507 per night

Flat in Key West

4.89 out of 5 average rating, 136 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

6–13 Oct

₹46,626 per night

Flat in Key West

4.92 out of 5 average rating, 175 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

16–23 Mar

₹59,875 per night

Guest favourite

Flat in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

3–10 Apr

₹25,436 per night

Guest favourite

Flat in Tavernier

5.0 out of 5 average rating, 15 reviews

Beautiful condo with a balcony

20–27 Jun

₹18,198 per night

Guest favourite

Flat in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

29 Aug – 5 Sep

₹59,247 per night

Guest favourite

Flat in Marathon

5.0 out of 5 average rating, 11 reviews

Beach Heaven-Private Beach, Pool

9–16 Sep

₹29,844 per night

House rentals with beach access

Guest favourite

Home in Marathon

4.9 out of 5 average rating, 136 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

5–12 Apr

₹28,279 per night

Guest favourite

Home in Key Colony Beach

4.96 out of 5 average rating, 134 reviews

Beautiful open plan remodeled home in Key Colony

27 Apr – 4 May

₹24,614 per night

Home in Cudjoe Key

4.86 out of 5 average rating, 43 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

10–17 Oct

₹41,555 per night

Home in Summerland Key

4.86 out of 5 average rating, 7 reviews

Bungalows at Sugarloaf Beach - Little Hammock

27 Dec – 3 Jan

₹52,190 per night

Home in Big Pine Key

4.92 out of 5 average rating, 13 reviews

Home in Big Pine Key

9–16 Feb

₹29,419 per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 17 reviews

Grouper Getaway @ Ocean Isles Fishing Village

8–15 May

₹13,497 per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

14–21 Dec

₹50,057 per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

31 Aug – 7 Sep

₹68,653 per night

Apartment rentals with beach access

Guest favourite

Apartment in Marathon

4.87 out of 5 average rating, 192 reviews

Sombrero Beach Tropical Getaway

9–16 Aug

₹17,533 per night

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

30 Aug – 6 Sep

₹22,786 per night

Guest favourite

Apartment in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

29 Sep – 6 Oct

₹35,566 per night

Guest favourite

Apartment in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

8–15 Nov

₹30,626 per night

Guest favourite

Apartment in Key Largo

4.98 out of 5 average rating, 115 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

7–14 Nov

₹41,535 per night

Guest favourite

Apartment in Tavernier

4.88 out of 5 average rating, 228 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

27 Aug – 3 Sep

₹20,927 per night

Guest favourite

Apartment in Key Largo

4.97 out of 5 average rating, 146 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

18–25 Feb

₹57,429 per night

Guest favourite

Apartment in Key West

4.83 out of 5 average rating, 243 reviews

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

27 Apr – 4 May

₹40,623 per night

Quick stats about holiday 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
₹11,677 before taxes and fees

Destinations to explore