Holiday rentals in Big Pine Key

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Top-rated holiday rentals in Big Pine Key

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Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 132 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

4–11 Jan

€ 637 per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

4–11 Jul

€ 240 per night

Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.

17–24 Nov

€ 121 per night

Guest favourite

Home in Ramrod Key

5.0 out of 5 average rating, 6 reviews

Canalfront 3BD/2BA|FLKeys|POOL|DOCK

Welcome to Casa Sirena, a canal-front paradise home in the peaceful lower Florida Keys. Enjoy the island breeze as soon as you arrive. You can enjoy a game of pool or sit & relax. Walk upstairs and catch sunset views from the outdoor balcony leading into the main entrance of the home. The Kitchen island offers additional seating for your guests along side the Dining Room table. Coffee lovers can enjoy a coffee station in the kitchen. Family kid games in the living room entertainment center.

7–14 Mar

€ 353 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.

24–31 Oct

€ 371 per night

Guest favourite

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!

27 Jan – 3 Feb

€ 539 per night

Superhost

Tiny home in Big Pine Key

4.84 out of 5 average rating, 31 reviews

Tiny Fish Haus

Come experience Tiny home living in this park model home that is located in a RV Condominium park in the Florida KEYS! We are located right next to a large outdoor pool, and have a ocean front park across the highway. Our outside patio has a sink and black stone grill. We also have a bonus shower outside to rinse off or cool down. Inside you will find premium West Elm bedding, Hot shower , kitchen with Stanley cookware, and a coffee press! Wi-Fi /Alexa and a mini washing machine.

26 Apr – 3 May

€ 216 per night

Superhost

Villa in Marathon

4.89 out of 5 average rating, 145 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

25 Aug – 1 Sep

€ 414 per night

Guest favourite

Campervan/Motorhome in Big Pine Key

4.89 out of 5 average rating, 44 reviews

You’re on island time at The Island Girl

Come and relax at our tropical escape. Only 33 miles North of Key West and 7 miles south of Bahia Honda beach. Our new 34’ Atlas RV is just what you need for a relaxing getaway. Walking distance of restaurants, grocery stores and Pine Channel Park. Enjoy biking, as well as walking to nearby charter services, kayak and boat launches. Extra amenities include a heated pool, laundry room, bath house and clubhouse facilities.Parking available for one vehicle and no trailers.

19–24 May

€ 247 per night

Guest favourite

Home in Marathon

4.96 out of 5 average rating, 123 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

22–29 Jul

€ 573 per night

Guest favourite

Campervan/Motorhome in Big Pine Key

4.93 out of 5 average rating, 40 reviews

Having fun in the lower Keys

Enjoy the lovely setting of this romantic spot in nature. Big Pine Key is in the center of the lower Keys just 35 miles from Key West making it convenient to all the tourism and night life adventure the Keys have to offer while simultaneously being far enough away to allow for an off the beaten path relaxing experience. I have left several destinations for diving , fishing and/or great spots to just relax and take in the sun.

25 Sep – 2 Oct

€ 185 per night

Superhost

Home in Cudjoe Key

4.88 out of 5 average rating, 188 reviews

Newly Renovated Oceanside House with Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

13–20 Sep

€ 387 per night