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Waterfront vacation 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, 42 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

Oct 10 – 17

R9,177 ZAR 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 3 – 10

R3,267 ZAR per night

Cottage in Little Torch Key

4.91 out of 5 average rating, 145 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!

Apr 25 – May 2

R10,170 ZAR 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.

Oct 24 – 31

R3,514 ZAR 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

R6,423 ZAR per night

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 83 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.

Jul 7 – 14

R3,871 ZAR 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

R6,838 ZAR 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 30 – Dec 7

R10,588 ZAR 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

R7,650 ZAR per night

Condo 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.”

Aug 22 – 29

R4,370 ZAR 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.

Apr 23 – 30

R10,217 ZAR per night

Home in Marathon

4.97 out of 5 average rating, 117 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.

May 22 – 29

R10,646 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

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Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Big Pine Key waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

Oct 22 – 29

R5,524 ZAR per night

Apartment in Key West

4.89 out of 5 average rating, 135 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Mar 7 – 14

R14,181 ZAR per night

Apartment in Key West

4.92 out of 5 average rating, 175 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

Jan 31 – Feb 7

R13,062 ZAR per night

Apartment in Key Largo

4.92 out of 5 average rating, 106 reviews

2/1 Oceanfront Apartment with Dockage

Apr 10 – 17

R6,888 ZAR per night

Apartment in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

Apr 3 – 10

R5,602 ZAR per night

Apartment in Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

Aug 24 – 31

R4,346 ZAR per night

Apartment in Marathon

4.95 out of 5 average rating, 38 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

Sep 20 – 27

R3,761 ZAR per night

Apartment in Marathon

5.0 out of 5 average rating, 5 reviews

Marathon Studio on Lovely Resort w/Amenities

Dec 25 – Jan 1

R7,319 ZAR 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

R6,301 ZAR per night

Home in Cudjoe Key

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

Oct 1 – 8

R4,222 ZAR per night

Home in Big Pine Key

4.82 out of 5 average rating, 62 reviews

Key home with open water access!!

Oct 2 – 9

R8,420 ZAR per night

Home in Key Colony Beach

4.98 out of 5 average rating, 51 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Apr 15 – 22

R5,114 ZAR per night

Home in Cudjoe Key

5.0 out of 5 average rating, 23 reviews

Paradise in Cudjoe! Perfect Family Home!

Oct 4 – 11

R7,249 ZAR per night

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

Aug 31 – Sep 7

R15,149 ZAR per night

Home in Big Pine Key

4.89 out of 5 average rating, 63 reviews

Fishermen`s Paradise

Dec 4 – 11

R18,737 ZAR per night

Home in Key Colony Beach

5.0 out of 5 average rating, 96 reviews

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

Feb 22 – Mar 1

R8,571 ZAR per night

Waterfront condo rentals

Condo in Key West

4.93 out of 5 average rating, 132 reviews

Beach Club Ocean Front 2BR Condo

Dec 1 – 8

R17,528 ZAR per night

Condo in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

Apr 14 – 21

R13,389 ZAR 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

R5,071 ZAR per night

Condo in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

May 31 – Jun 7

R3,911 ZAR 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

R7,853 ZAR 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

Jan 24 – 31

R7,162 ZAR 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

R9,149 ZAR 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

Feb 16 – 23

R9,491 ZAR 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
R1,880 ZAR before taxes and fees

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