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Vacation 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

4.9 out of 5 average rating, 135 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!

Dec 14 – 21

G$181,350 GYD per night

Guest suite in Marathon

4.98 out of 5 average rating, 186 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.

Jul 28 – Aug 4

G$45,279 GYD per night

Tiny home in Big Pine Key

4.81 out of 5 average rating, 93 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.

Apr 20 – 27

G$31,761 GYD 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.

Sep 23 – 30

G$83,266 GYD per night

Tiny home in Big Pine Key

4.85 out of 5 average rating, 33 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.

Sep 23 – 30

G$38,971 GYD 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.

Aug 21 – 28

G$71,210 GYD per night

Villa in Marathon

4.89 out of 5 average rating, 148 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!

Oct 11 – 18

G$78,772 GYD 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 25 – Nov 1

G$81,042 GYD 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

G$75,299 GYD 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.”

Nov 9 – 16

G$48,448 GYD per night

Apartment in Key West

4.92 out of 5 average rating, 1055 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.

Nov 14 – 21

G$66,768 GYD per night

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise and 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."

Sep 27 – Oct 4

G$77,384 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

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Hotels

Stylish accommodations and amenities

Popular amenities for Big Pine Key rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Key West

4.94 out of 5 average rating, 272 reviews

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

Mar 29 – Apr 5

G$117,855 GYD per night

Home in Key Colony Beach

4.96 out of 5 average rating, 136 reviews

Beautiful open plan remodeled home in Key Colony

Nov 11 – 18

G$48,316 GYD per night

Home in Key Colony Beach

4.81 out of 5 average rating, 132 reviews

Waterview from three sides, Cabana Club, 30' Docks

Jan 10 – 17

G$81,179 GYD per night

Home in Key Colony Beach

4.92 out of 5 average rating, 88 reviews

Paradise in Key Colony Beach + Cabana Club

Nov 9 – 16

G$31,284 GYD per night

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Mar 29 – Apr 5

G$125,952 GYD per night

Home in Big Pine Key

4.89 out of 5 average rating, 64 reviews

Fishermen`s Paradise

Dec 4 – 11

G$207,734 GYD per night

Home in Marathon

4.98 out of 5 average rating, 85 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

Nov 2 – 9

G$94,436 GYD per night

Home in Cudjoe Key

4.87 out of 5 average rating, 46 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Dec 1 – 8

G$155,267 GYD per night

Condo rentals with a pool

Condo in Marathon

4.87 out of 5 average rating, 193 reviews

Sombrero Beach Tropical Getaway

Nov 13 – 20

G$46,954 GYD per night

Condo in Key West

4.89 out of 5 average rating, 148 reviews

Large waterfront 2/2 end unit with boat slip

Sep 5 – 12

G$119,217 GYD per night

Condo in Key West

4.86 out of 5 average rating, 130 reviews

A Perfect Getaway

Aug 20 – 27

G$75,780 GYD 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

G$105,222 GYD per night

Condo in Marathon

5.0 out of 5 average rating, 7 reviews

Ocean Potion NEW 1B/2B 3Balconies Ocean View

May 26 – Jun 2

G$48,656 GYD per night

Condo in Key Colony Beach

5.0 out of 5 average rating, 27 reviews

Sea-Esta Condo beach and pool

Nov 9 – 16

G$48,211 GYD per night

Condo in Marathon

4.97 out of 5 average rating, 74 reviews

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

Oct 16 – 23

G$40,200 GYD per night

Condo in Marathon

4.94 out of 5 average rating, 94 reviews

Discounted! Waterfront, Pool, Tiki Bar and Marina!

Oct 16 – 23

G$59,864 GYD per night

Quick stats about vacation 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
2.5K reviews
Nightly prices starting at
G$16,678 GYD before taxes and fees

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