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Waterfront vacation rentals in Summerland Key

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Top-rated waterfront rentals in Summerland Key

Guests agree: these waterfront rentals 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

Aug 19 – 26

€ 425 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.

Mar 9 – 16

€ 399 per night

Vacation 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

Sep 19 – 26

€ 225 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.

Sep 5 – 12

€ 193 per night

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!

Sep 6 – 13

€ 523 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.

Apr 8 – 15

€ 202 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.

Oct 29 – Nov 5

€ 369 per night

Home in Cudjoe Key

4.97 out of 5 average rating, 121 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.

Oct 7 – 14

€ 387 per night

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.

Aug 24 – 31

€ 470 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!

Apr 14 – 21

€ 474 per night

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.

Oct 1 – 8

€ 250 per night

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.

Nov 3 – 10

€ 616 per night

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Popular amenities for Summerland Key waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Key Largo

4.98 out of 5 average rating, 125 reviews

Key Largo Kawama Lagoon Free Cancel Deutsch Spain

Jul 29 – Aug 5

€ 335 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

€ 589 per night

Apartment in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

Apr 11 – 18

€ 454 per night

Apartment in Key West

4.92 out of 5 average rating, 175 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

Mar 16 – 23

€ 766 per night

Apartment in Key Largo

4.92 out of 5 average rating, 106 reviews

2/1 Oceanfront Apartment with Dockage

Jul 2 – 9

€ 434 per night

Apartment in Key Largo

4.76 out of 5 average rating, 185 reviews

Hideaway with Picturesque Canal View Apt 3

Oct 15 – 22

€ 267 per night

Apartment in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

Apr 3 – 10

€ 335 per night

Apartment in Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

Sep 19 – 26

€ 272 per night

Waterfront house rentals

Home in Marathon

4.9 out of 5 average rating, 136 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Apr 5 – 12

€ 377 per night

Home in Cudjoe Key

4.86 out of 5 average rating, 43 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Oct 10 – 17

€ 533 per night

Home in Cudjoe Key

5.0 out of 5 average rating, 23 reviews

Paradise in Cudjoe! Perfect Family Home!

Oct 4 – 11

€ 431 per night

Home in Summerland Key

4.83 out of 5 average rating, 6 reviews

Bungalows at Sugarloaf Beach - Little Hammock

Dec 27 – Jan 3

€ 714 per night

Home in Big Pine Key

4.92 out of 5 average rating, 13 reviews

Home in Big Pine Key

Feb 9 – 16

€ 369 per night

Home in Cudjoe Key

5.0 out of 5 average rating, 7 reviews

Venture Out- Million Dollar Island Resort

Nov 30 – Dec 7

€ 376 per night

Home in Cudjoe Key

4.82 out of 5 average rating, 49 reviews

Spanish Queen @Venture Out

Aug 18 – 25

€ 428 per night

Home in Cudjoe Key

4.95 out of 5 average rating, 19 reviews

Conch Cabana in Paradise 23 miles outside Key West

Mar 27 – Apr 3

€ 385 per night

Waterfront condo rentals

Condo in Key Colony Beach

4.81 out of 5 average rating, 108 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

Nov 2 – 9

€ 253 per night

Condo in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

Nov 8 – 15

€ 872 per night

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Aug 30 – Sep 6

€ 288 per night

Condo in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

Sep 29 – Oct 6

€ 460 per night

Condo in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

Nov 8 – 15

€ 399 per night

Condo in Key Largo

4.98 out of 5 average rating, 115 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

Nov 7 – 14

€ 536 per night

Condo in Key West

4.85 out of 5 average rating, 143 reviews

Anchor Drop modern elegance upgrades throughout vi

Sep 15 – 22

€ 550 per night

Condo in Tavernier

4.93 out of 5 average rating, 133 reviews

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

Feb 14 – 21

€ 444 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
2.2K reviews
Nightly prices starting at
€ 103 before taxes and fees

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