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Waterfront vacation rentals in Sugarloaf Key

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Top-rated waterfront rentals in Sugarloaf 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

Home in Key Largo

4.98 out of 5 average rating, 121 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!!!

Sep 7 – 14

ﺩ.ﺇ741 per night

Condo in Key Colony Beach

4.96 out of 5 average rating, 171 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Nov 18 – 25

ﺩ.ﺇ1,376 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 West

4.89 out of 5 average rating, 148 reviews

Large waterfront 2/2 end unit with boat slip

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grills, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Mar 22 – 29

ﺩ.ﺇ2,670 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

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

Townhouse in Key West

4.91 out of 5 average rating, 109 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Nov 23 – 30

ﺩ.ﺇ1,601 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

Tiny home in Key Largo

4.98 out of 5 average rating, 167 reviews

The Oasis in key largo with your own private beach

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people and one paddle board. There is also a community pool for your enjoyment. Fishing rods are available for use.

Jan 15 – 22

ﺩ.ﺇ1,054 per night

Vacation rentals for every style

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Popular amenities for Sugarloaf Key waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Key Largo

4.92 out of 5 average rating, 231 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Dec 7 – 14

ﺩ.ﺇ720 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 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 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 Largo

4.75 out of 5 average rating, 186 reviews

Hideaway with Picturesque Canal View Apt 3

Jun 6 – 13

ﺩ.ﺇ649 per night

Apartment in Key Largo

4.98 out of 5 average rating, 126 reviews

Key Largo Kawama Lagoon Free Cancel Deutsch Spain

Aug 15 – 22

ﺩ.ﺇ1,167 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.ﺇ1,301 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

Waterfront house rentals

Home in Marathon

4.97 out of 5 average rating, 119 reviews

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

Dec 20 – 27

ﺩ.ﺇ2,469 per night

Home in Upper Sugarloaf Key

4.87 out of 5 average rating, 46 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Oct 28 – Nov 4

ﺩ.ﺇ3,578 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

4.87 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

4.82 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

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

Oct 1 – 8

ﺩ.ﺇ842 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

Waterfront condo rentals

Condo in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Oct 27 – Nov 3

ﺩ.ﺇ871 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 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

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

Apr 22 – 29

ﺩ.ﺇ1,340 per night

Condo in Key Largo

4.98 out of 5 average rating, 117 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

Nov 2 – 9

ﺩ.ﺇ1,829 per night

Condo in Tavernier

4.93 out of 5 average rating, 136 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

4.83 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

Destinations to explore