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

Airbnb your place

Waterfront holiday rentals in Summerland Key

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Summerland Key

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

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

Houseboat in Key West

4.81 out of 5 average rating, 254 reviews

Key West Houseboat Paradise

56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats. The property has an fairly industrial feel to it with a 2-bay local garage/taxi company on site so Shore Side is nuthin' fancy but the back deck looks out on mangrove islands dotting Boca Chica Channel with two 12' Sea Kayaks ready to go.

9–16 Mar

₹32,658 per night

Guest favourite

Holiday home in Key Largo

4.99 out of 5 average rating, 145 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

19–26 Sep

₹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

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!

6–13 Sep

₹40,704 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

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

4.97 out of 5 average rating, 122 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.

7–14 Oct

₹30,973 per night

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 106 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.

24–31 Aug

₹34,714 per night

Home in Cudjoe Key

4.81 out of 5 average rating, 220 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!

14–21 Apr

₹36,206 per night

Guest favourite

Home in Cudjoe Key

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

Wow!!! Our new spacious 3 bedrooms, 2 full bath home on a 60-foot wide, deep-water canal with a 60-foot-long dock is only 1,500 feet from the open waters of Kemp Channel. Our canal enters Kemp Channel just to the north of the Overseas Highway Bridge, so that our guests bringing their boats have access to the Atlantic Ocean and the Gulf of Mexico. We have a guest friendly cancellation policy as described below in this listing.

1–8 Oct

₹19,127 per night

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.

3–10 Nov

₹46,179 per night

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for waterfront rentals in Summerland Key

Free parking on premises

Air conditioning

Waterfront apartment rentals

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

Guest favourite

Flat in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

11–18 Apr

₹35,128 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 Key Largo

4.92 out of 5 average rating, 106 reviews

2/1 Oceanfront Apartment with Dockage

2–9 Jul

₹33,888 per night

Flat in Key Largo

4.76 out of 5 average rating, 185 reviews

Hideaway with Picturesque Canal View Apt 3

15–22 Oct

₹20,388 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 Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

19–26 Sep

₹19,711 per night

Waterfront house rentals

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

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

Guest favourite

Home in Cudjoe Key

5.0 out of 5 average rating, 23 reviews

Paradise in Cudjoe! Perfect Family Home!

4–11 Oct

₹32,894 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

Home in Cudjoe Key

5.0 out of 5 average rating, 7 reviews

Venture Out- Million Dollar Island Resort

30 Nov – 7 Dec

₹26,749 per night

Home in Cudjoe Key

4.82 out of 5 average rating, 49 reviews

Spanish Queen @Venture Out

18–25 Aug

₹32,618 per night

Guest favourite

Home in Cudjoe Key

4.95 out of 5 average rating, 19 reviews

Conch Cabana in Paradise 23 miles outside Key West

27 Mar – 3 Apr

₹28,332 per night

Waterfront apartment rentals

Apartment in Key Colony Beach

4.81 out of 5 average rating, 108 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

2–9 Nov

₹19,787 per night

Guest favourite

Apartment in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

8–15 Nov

₹68,234 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 Key West

4.85 out of 5 average rating, 143 reviews

Anchor Drop modern elegance upgrades throughout vi

15–22 Sep

₹41,473 per night

Guest favourite

Apartment in Tavernier

4.93 out of 5 average rating, 133 reviews

It's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba

14–21 Feb

₹35,784 per night

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
2.2T reviews
Nightly prices starting at
₹9,175 before taxes and fees

Destinations to explore