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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

Jul 12 – 19

ﺩ.ﺇ1,505 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!

Feb 4 – 11

ﺩ.ﺇ2,027 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.

Dec 14 – 21

ﺩ.ﺇ701 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.

Apr 4 – 11

ﺩ.ﺇ2,037 per night

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.

Oct 14 – 21

ﺩ.ﺇ1,606 per night

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.

Nov 6 – 13

ﺩ.ﺇ2,054 per night

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.

Sep 14 – 21

ﺩ.ﺇ1,528 per night

Home in Cudjoe Key

4.81 out of 5 average rating, 221 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!

Aug 22 – 29

ﺩ.ﺇ1,509 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

ﺩ.ﺇ842 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.

Dec 1 – 8

ﺩ.ﺇ2,033 per night

Home in Marathon

4.97 out of 5 average rating, 118 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.

Dec 20 – 27

ﺩ.ﺇ2,469 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.

Oct 10 – 17

ﺩ.ﺇ2,513 per night

Vacation rentals for every style

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Popular amenities for Summerland Key waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Tavernier

4.95 out of 5 average rating, 149 reviews

Boho FL Keys Condo

Oct 10 – 17

ﺩ.ﺇ1,102 per night

Apartment in Key West

4.92 out of 5 average rating, 175 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

Dec 8 – 15

ﺩ.ﺇ2,412 per night

Apartment in Key Largo

4.92 out of 5 average rating, 106 reviews

2/1 Oceanfront Apartment with Dockage

Apr 10 – 17

ﺩ.ﺇ1,298 per night

Apartment in Key West

4.89 out of 5 average rating, 136 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Dec 10 – 17

ﺩ.ﺇ2,135 per night

Apartment in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

Jul 15 – 22

ﺩ.ﺇ1,261 per night

Apartment in Key Largo

4.78 out of 5 average rating, 137 reviews

Escape to the Seaside!

Jul 28 – Aug 2

ﺩ.ﺇ1,517 per night

Apartment in Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

Dec 3 – 10

ﺩ.ﺇ868 per night

Apartment in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

Aug 12 – 19

ﺩ.ﺇ2,609 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 12 – 19

ﺩ.ﺇ975 per night

Home in Cudjoe Key

5.0 out of 5 average rating, 23 reviews

Paradise in Cudjoe! Perfect Family Home!

Oct 4 – 11

ﺩ.ﺇ1,450 per night

Home in Cudjoe Key

5.0 out of 5 average rating, 7 reviews

Venture Out- Million Dollar Island Resort

Dec 7 – 14

ﺩ.ﺇ1,178 per night

Home in Cudjoe Key

4.82 out of 5 average rating, 49 reviews

Spanish Queen @Venture Out

Jan 6 – 13

ﺩ.ﺇ1,436 per night

Home in Cudjoe Key

4.95 out of 5 average rating, 19 reviews

Conch Cabana in Paradise 23 miles outside Key West

Jan 13 – 20

ﺩ.ﺇ1,149 per night

Home in Cudjoe Key

4.87 out of 5 average rating, 45 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Mar 3 – 10

ﺩ.ﺇ2,792 per night

Home in Cudjoe Key

4.86 out of 5 average rating, 28 reviews

Keys Island Villa - Venture Out Home 354

Oct 8 – 15

ﺩ.ﺇ1,545 per night

Home in Cudjoe Key

4.83 out of 5 average rating, 12 reviews

Rise-N-Shine

Feb 9 – 16

ﺩ.ﺇ1,928 per night

Waterfront condo rentals

Condo in Key West

4.89 out of 5 average rating, 148 reviews

Large waterfront 2/2 end unit with boat slip

Mar 22 – 29

ﺩ.ﺇ2,670 per night

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Sep 21 – 28

ﺩ.ﺇ982 per night

Condo in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

Apr 1 – 8

ﺩ.ﺇ2,036 per night

Condo in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

Apr 22 – 29

ﺩ.ﺇ1,340 per night

Condo in Tavernier

4.93 out of 5 average rating, 135 reviews

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

Feb 20 – 27

ﺩ.ﺇ1,566 per night

Condo in Key West

4.85 out of 5 average rating, 143 reviews

Anchor Drop modern elegance upgrades throughout vi

Mar 10 – 17

ﺩ.ﺇ3,977 per night

Condo in Tavernier

4.91 out of 5 average rating, 111 reviews

500 Burton Drive Tavernier, Key Largo

Oct 7 – 14

ﺩ.ﺇ997 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

Apr 24 – May 1

ﺩ.ﺇ1,893 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
ﺩ.ﺇ404 before taxes and fees

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