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Holiday rentals with a pool in Big Pine Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Big Pine Key

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Cottage in Cudjoe Key

4.91 out of 5 average rating, 133 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!

3–10 Mar

₹72,583 per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 185 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.

12–19 Oct

₹18,122 per night

Tiny home in Big Pine Key

4.8 out of 5 average rating, 89 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.

6–13 Jun

₹9,847 per night

Home in Cudjoe Key

4.9 out of 5 average rating, 104 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

17–24 Jan

₹33,326 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.

10–17 Aug

₹28,501 per night

Guest favourite

Guest house in Key West

4.93 out of 5 average rating, 527 reviews

Old Town - Room Opens to Pool and Garden

Located in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

22–29 Jun

₹28,165 per night

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!

3–10 Apr

₹36,764 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.

7–14 Oct

₹30,341 per night

Guest favourite

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.

24–31 Aug

₹33,946 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

₹19,391 per night

Guest favourite

Flat in Key West

4.92 out of 5 average rating, 1036 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

28 Jul – 4 Aug

₹23,687 per night

Guest favourite

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise at Cudjoe Bay

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

15–22 Jan

₹33,747 per night

Holiday rentals for every style

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Stylish accommodation and amenities

Popular amenities for Big Pine Key rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Key West

4.94 out of 5 average rating, 272 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

2–9 Apr

₹47,170 per night

Guest favourite

Home in Key Colony Beach

4.96 out of 5 average rating, 135 reviews

Beautiful open plan remodeled home in Key Colony

27 Apr – 4 May

₹24,099 per night

Home in Cudjoe Key

4.86 out of 5 average rating, 43 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

10–17 Oct

₹40,720 per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

14–21 Dec

₹49,023 per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 17 reviews

Grouper Getaway @ Ocean Isles Fishing Village

8–15 May

₹13,191 per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

31 Aug – 7 Sep

₹67,220 per night

Guest favourite

Home in Big Pine Key

4.89 out of 5 average rating, 63 reviews

Fishermen`s Paradise

4–11 Dec

₹83,143 per night

Guest favourite

Home in Little Torch Key

4.88 out of 5 average rating, 57 reviews

Waterfront Beach House with Dock & Heated Pool!

29 Sep – 6 Oct

₹71,965 per night

Apartment rentals with a pool

Guest favourite

Apartment in Key West

4.93 out of 5 average rating, 132 reviews

Beach Club Ocean Front 2BR Condo

1–8 Dec

₹77,776 per night

Guest favourite

Apartment in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

8–15 Nov

₹66,868 per night

Guest favourite

Apartment in Key West

4.86 out of 5 average rating, 129 reviews

A Perfect Getaway

8–15 Dec

₹37,100 per night

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

30 Aug – 6 Sep

₹22,321 per night

Guest favourite

Apartment in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

11–18 Dec

₹34,846 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

₹40,613 per night

Guest favourite

Apartment in Tavernier

4.88 out of 5 average rating, 228 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

30 Jul – 6 Aug

₹20,734 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

27 Apr – 4 May

₹39,800 per night

Quick stats about holiday rentals with a pool in Big Pine Key

Total rentals
100 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
2.5T reviews
Nightly prices starting at
₹6,675 before taxes and fees

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