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Waterfront holiday rentals in Summerland Key

Find and book unique waterfront accommodation on Airbnb

Top-rated waterfront accommodation in Summerland Key

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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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

7 – 14 July

$4,795 AUD total

Guest favourite

Cottage in Little Torch Key

4.91 out of 5 average rating, 146 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

25 Apr – 2 May

$6,640 AUD total

Guest favourite

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.

27 Jan – 3 Feb

$6,545 AUD total

Home in Cudjoe Key

4.82 out of 5 average rating, 49 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $113 directly to security upon entry into the park***

16 – 23 Dec

$4,827 AUD total

Guest favourite

Home in Cudjoe Key

4.97 out of 5 average rating, 124 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

2 – 9 Sept

$3,563 AUD total

Guest favourite

Townhouse in Marathon

4.97 out of 5 average rating, 116 reviews

Boater’s Paradise 3br/2.5ba waterfront with slip!

Spectacular PET FRIENDLY 3 bed/2.5 bath 1350sf villa in beautiful Coral Lagoon, complete with a 40 foot wet slip and all the amenities! Spread out and enjoy the spacious, clean interior with free high speed wifi. Step outside to your boat and enjoy all the Gulf and Atlantic have to offer - both easily accessible in minutes. Relax with a drink at the pool after a long day of fun in the sun. NEW in 2021! Mattresses, bedding, towels, appliances, paint, grill, dinnerware.

2 – 9 Dec

$6,657 AUD total

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 107 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

14 – 21 Sept

$4,786 AUD total

Home in Cudjoe Key

4.81 out of 5 average rating, 222 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

16 – 23 Dec

$5,945 AUD total

Guest favourite

Townhouse in Marathon

4.97 out of 5 average rating, 146 reviews

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For your safety, the entire house is sanitized prior to your arrival. Along with our standard cleaning practices we have a local company that comes in and fogs the entire house with hospital grade sanitizer.

12 – 19 Sept

$6,956 AUD total

Guest favourite

Home in Marathon

4.98 out of 5 average rating, 120 reviews

Marathon one-level home on the Marina - with slip!

***New Listing! Recently renovated with all new furnishings and appliances*** Beautiful oasis in the heart of the Florida Keys, Marathon is a fisherman's paradise. Coral Lagoon is the perfect destination for a relaxing family getaway and this home is all new with stylish interior and unbeatable location.

23 – 30 Dec

$8,124 AUD total

Guest favourite

Houseboat in Key West

4.91 out of 5 average rating, 194 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.

28 Mar – 4 Apr

$8,153 AUD total

Holiday rentals for every style

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Popular amenities for Summerland Key waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment accommodation

Apartment in Key West

4.92 out of 5 average rating, 175 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

20 – 27 Dec

$10,056 AUD total

Apartment in Key West

4.89 out of 5 average rating, 136 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

10 – 17 Dec

$6,895 AUD total

Guest favourite

Apartment in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

28 Sept – 5 Oct

$8,256 AUD total

Guest favourite

Apartment in Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

26 Nov – 3 Dec

$3,067 AUD total

Apartment in Key Colony Beach

4.84 out of 5 average rating, 79 reviews

Beachside Unit 22 - Private Beach on Atlantic

1 – 8 Sept

$2,742 AUD total

Apartment in Key West

4.89 out of 5 average rating, 46 reviews

Penthouse in Paradise

30 May – 6 June

$6,934 AUD total

Guest favourite

Apartment in Marathon

4.95 out of 5 average rating, 38 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

30 Oct – 6 Nov

$3,147 AUD total

Guest favourite

Apartment in Marathon

5.0 out of 5 average rating, 5 reviews

Marathon Studio on Lovely Resort w/Amenities

25 Dec – 1 Jan

$4,608 AUD total

Waterfront house rentals

Guest favourite

Home in Marathon

4.9 out of 5 average rating, 137 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

12 – 19 Apr

$3,531 AUD total

Guest favourite

Home in Key Colony Beach

4.96 out of 5 average rating, 136 reviews

Beautiful open plan remodeled home in Key Colony

20 – 27 Oct

$2,654 AUD total

Home in Cudjoe Key

5.0 out of 5 average rating, 7 reviews

Venture Out- Million Dollar Island Resort

31 Aug – 7 Sept

$4,241 AUD total

Home in Cudjoe Key

4.87 out of 5 average rating, 46 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

24 – 31 Aug

$8,361 AUD total

Home in Cudjoe Key

4.86 out of 5 average rating, 28 reviews

Keys Island Villa - Venture Out Home 354

11 – 18 Oct

$5,109 AUD total

Guest favourite

Home in Cudjoe Key

4.95 out of 5 average rating, 19 reviews

Conch Cabana in Paradise 23 miles outside Key West

13 – 20 Apr

$5,122 AUD total

Guest favourite

Home in Cudjoe Key

4.83 out of 5 average rating, 12 reviews

Rise-N-Shine

3 – 10 Apr

$6,370 AUD total

Home in Cudjoe Key

4.92 out of 5 average rating, 12 reviews

Waterfront 35’ Dock,80’ pool,20 min Key West

11 – 18 Oct

$4,018 AUD total

Waterfront condo accommodation

Guest favourite

Condo in Key West

4.89 out of 5 average rating, 148 reviews

Large waterfront 2/2 end unit with boat slip

13 – 20 Feb

$8,788 AUD total

Guest favourite

Condo in Key West

4.85 out of 5 average rating, 143 reviews

Anchor Drop modern elegance upgrades throughout vi

10 – 17 Mar

$13,019 AUD total

Guest favourite

Condo in Key West

4.83 out of 5 average rating, 243 reviews

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

24 Apr – 1 May

$6,009 AUD total

Guest favourite

Condo in Key Colony Beach

5.0 out of 5 average rating, 27 reviews

Sea-Esta Condo beach and pool

9 – 16 Nov

$2,866 AUD total

Guest favourite

Condo in Key West

4.96 out of 5 average rating, 76 reviews

Hidden Beach unit 1 The Perfect Place to stay

27 Nov – 4 Dec

$6,931 AUD total

Guest favourite

Condo in Key West

5.0 out of 5 average rating, 30 reviews

Gorgeous Ocean View in Paradise

31 Aug – 7 Sept

$6,762 AUD total

Guest favourite

Condo in Marathon

5.0 out of 5 average rating, 7 reviews

Ocean Potion NEW 1B/2B 3Balconies Ocean View

20 – 27 Dec

$5,945 AUD total

Guest favourite

Condo in Key West

4.98 out of 5 average rating, 47 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

22 – 29 Aug

$8,228 AUD total

Quick stats about waterfront rentals in Summerland Key

Total rentals
120 properties
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
2.2K reviews
Nightly prices starting at
$167 AUD before taxes and fees

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