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Waterfront holiday rentals in Big Pine Key

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Top-rated waterfront rentals in Big Pine Key

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

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Home in Cudjoe Key

4.86 out of 5 average rating, 43 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there. Also see our other paradise, http://airbnb.com/h/keysshangrila

12–19 Sep

$953 SGD per night

Guest favourite

Apartment 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.

13–20 Nov

$474 SGD 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!

9–16 Apr

$751 SGD 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.

7–14 Aug

$248 SGD per night

Guest favourite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 84 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

17–24 Sep

$254 SGD 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.

29 Aug – 5 Sep

$514 SGD per night

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.

6–13 Nov

$761 SGD per night

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.

24–31 Aug

$503 SGD per night

Guest favourite

Apartment in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Unit 39 Details: Second Floor Unit, Tub with Shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

22–29 Aug

$323 SGD per night

Guest favourite

Home in Marathon

4.9 out of 5 average rating, 136 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

5–12 Apr

$464 SGD 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

$312 SGD 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.

27 Apr – 4 May

$805 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

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

Hotels

Stylish accommodation and amenities

Popular amenities for waterfront rentals in Big Pine Key

Free parking on premises

Air conditioning

Waterfront apartment rentals

Flat in Key West

4.89 out of 5 average rating, 136 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

6–13 Oct

$760 SGD per night

Flat in Key West

4.92 out of 5 average rating, 175 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

10–17 Mar

$976 SGD per night

Guest favourite

Flat in Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

11–18 Nov

$321 SGD per night

Guest favourite

Flat in Marathon

5.0 out of 5 average rating, 5 reviews

Marathon Studio on Lovely Resort w/Amenities

25 Dec – 1 Jan

$540 SGD per night

Guest favourite

Flat in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

30 Sep – 7 Oct

$966 SGD per night

Guest favourite

Flat in Marathon

4.95 out of 5 average rating, 38 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

7–14 Mar

$661 SGD per night

Flat in Key West

4.89 out of 5 average rating, 45 reviews

Penthouse in Paradise

8–15 Oct

$638 SGD per night

Flat in Key West

5.0 out of 5 average rating, 4 reviews

Partial ocean view studio with king bed

12–19 Apr

$511 SGD per night

Waterfront house rentals

Guest favourite

Home in Key Colony Beach

4.98 out of 5 average rating, 51 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

6–13 Oct

$354 SGD per night

Guest favourite

Home in Big Pine Key

4.89 out of 5 average rating, 63 reviews

Fishermen`s Paradise

4–11 Dec

$1,384 SGD 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

$537 SGD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

31 Aug – 7 Sep

$1,119 SGD per night

Guest favourite

Home in Key Colony Beach

5.0 out of 5 average rating, 96 reviews

ABeachBungalow-60’dock w/ access to pool and beach

19–26 Apr

$633 SGD per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 36 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

6–13 Oct

$634 SGD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 10 reviews

Canal Front, Boat Dock, Updated!

11–18 Aug

$208 SGD per night

Home in Marathon

4.94 out of 5 average rating, 35 reviews

Gorgeous Ocean View Home!

4–11 Apr

$664 SGD per night

Waterfront apartment rentals

Guest favourite

Apartment in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

9–16 Sep

$794 SGD 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

$676 SGD per night

Guest favourite

Apartment in Key West

4.83 out of 5 average rating, 243 reviews

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

28 Oct – 4 Nov

$536 SGD per night

Guest favourite

Apartment in Key Colony Beach

5.0 out of 5 average rating, 27 reviews

Sea-Esta Condo beach and pool

9–16 Nov

$321 SGD per night

Guest favourite

Apartment in Marathon

4.93 out of 5 average rating, 14 reviews

Paradise Palms NEW 1B/2B Desk; Pool; Balcony

10–17 Jul

$318 SGD per night

Guest favourite

Apartment in Key West

4.96 out of 5 average rating, 76 reviews

Hidden Beach unit 1 The Perfect Place to stay

2–9 Dec

$848 SGD per night

Apartment in Marathon

4.89 out of 5 average rating, 18 reviews

Paradise @ MM61 - Waterfront 1 BR / 1 Bath Condo

3–10 Jan

$281 SGD per night

Guest favourite

Apartment in Marathon

4.97 out of 5 average rating, 74 reviews

NAUTI HIDEAWAY-Deep Slip/Ramp/Trailer Parking/Pool

2–9 Apr

$346 SGD per night

Quick stats about waterfront rentals in Big Pine Key

Total rentals
120 properties
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
2K reviews
Nightly prices starting at
$136 SGD before taxes and fees

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