
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.

Sea Ray Cove w/ 80' Dock, Pool, Beach & Tiki Hut
2025 - New concrete dock, fenders & fish filet table. 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.

Beautiful Cottage & Amenities in Gated Community
Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
7 DAY MINIMUM BOOKINGS / MAX 4 PERSONS NAUTI HIDEAWAY - This Nauti Stays Vacation Rental property is a 2-bedroom, 2-bath 2nd level 925 sq ft. condo located in Coco Plum, Marathon. Set in a well-protected, deep canal on the Atlantic, comes with a deep slip (length up to 40 ft) next to pool allowing access to the Atlantic Ocean and Florida Bay. ONSITE boat ramp & trailer (36 ft max) parking! Enjoy a heated or chilled pool after a boat day! Dock has water, power hook ups & fish cleaning station.

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

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.

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

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!

Beachside Unit 33-Private Tropical Beach Plus Pool
Unit 33 Details: Second Floor, Walk-in 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.”

Paradise in Key Colony Beach + Cabana Club
Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Tiny Fish Haus
Great location in the lower keys , 28 miles to Key West..8 miles to Bahia Honda State Park and right next to the National Key Deer Refuge! Relax on our covered patio next to a large Swimming Pool, Cook dinner on a Blackstone grill and enjoy WIFI, Games, a Flat Screen TV , we have Premium Organic Bedding on our Queen beds for comfort. Turkish Towels for bath and beach..Explore Big Pine Key with our 2 beach cruiser bicycles!

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.
Popular amenities for Big Pine Key rentals with a pool
House rentals with a pool

Discount Available! Pool 100' Dock, Fun Amenities!

Grouper Getaway @ Ocean Isles Fishing Village

Florida Keys Retreat

Tiki Time in Cudjoe Key 136

Waterfront Beach House with Dock & Heated Pool!

Fisherman's Paradise Cudjoe Key

Waterfront House with 37 ft Dock & Cabana Club

Bohemian Beach Bungalow
Condo rentals with a pool

Canal View Condo w/ Pool, Balcony & Bar

Tropical Escape at Sunrise

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Private Beach in Marathons Key Colony Beach

Fully renovated 2/2 bath condo w/ shared pool!

Scenic Oceanview Haven | Pool & Beach Access #7

Paradise found! Sea-Esta Condo beach and pool.

Sandy Toes Approved — Studio Beach Escape
Other vacation rentals with a pool

Waterfront, Dock, Pool, Pickleball, near Key West!

Keys Island Villa - Venture Out Home 354

Updated Key Colony Tiki Hut-37.5 Dock-Cabana Club

Secluded Waterfront home, Views, Dock, Amenities,

Ocean Isles #98~ Fishing Village, Community Pool!

Discount - Jan 31! 3 Bed/3 BA Cabana Club Access!

Ocean~View*Pool*Dock*Kayaks*King Bed

Island Girl Big Pine Key
When is the best time to visit Big Pine Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R4,045 ZAR | R3,820 ZAR | R3,868 ZAR | R3,626 ZAR | R3,368 ZAR | R3,868 ZAR | R4,303 ZAR | R4,271 ZAR | R3,094 ZAR | R2,417 ZAR | R2,788 ZAR | R2,998 ZAR |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
Quick stats about vacation rentals with a pool in Big Pine Key

Total vacation rentals
Explore 110 vacation rentals in Big Pine Key

Nightly prices starting at
Big Pine Key vacation rentals start at R1,128 ZAR per night before taxes and fees

Verified guest reviews
Over 2,850 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
110 of Big Pine Key vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Big Pine Key rentals

4.8 Average rating
Big Pine Key stays are highly rated by guests—averaging 4.8 out of 5!
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- Key West Lighthouse Museum
- Ernest Hemingway Home & Museum
- Sombrero Beach
- Smathers Beach
- The Turtle Hospital
- Calusa Beach & Loggerhead Beach
- History Of Diving Museum
- Sea Oats Beach
- Conch Key
- Long Beach
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Sunset Park
- Florida Keys Aquarium Encounters
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Dolphin Research Center
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Boyd's Key West Campground




