
Holiday rentals with a pool in Sunset Key
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Top-rated rentals with a pool in Sunset Key
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King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.
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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!
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Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.
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Historic Cigar House. 3rd floor Suite W/Kitchen
This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.
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Gorgeous Ocean View in Paradise, Close to Key West
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.
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Penthouse in Paradise
Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.
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Waterfront Dock Pool Condo Near Duval St Pet OK
Bring friends and family to this spacious 1,350 sq ft waterfront corner condo in historic downtown Key West. Enjoy a full kitchen, open living space, and a private balcony with marina and pool views. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, and Hemingway House. Amenities include a heated pool, tiki area, BBQ grills, parking, elevator, and secure entry.
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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.
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Palm Breezes! Room for Everyone on the Ocean.
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.
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*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.
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Affordable Beachfront Luxury Condo Sleeps 6
My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!
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Duval Street Suites full kitchen and heated pool
The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking the pool in historic Old Town, Key West. Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.
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Popular amenities for Sunset Key rentals with a pool
House rentals with a pool

Pool Access + Local Art • Walk to Southernmost
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KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK
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Gorgeous Romantic Private Villa, Steps from Duval!
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White House - Receive $400 towards a Boat Rental!
LocationFamilyPool

Paradise found
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AUG/SEPT. Save$ Oceanfront 4 BIKE/2 Kayak KING Bed
ValueFamilySleep quality

Waterfront Beach House with Dock & Heated Pool!
FamilyLocationBeach

Betty's Place
FamilyValueAir conditioning
Apartment rentals with a pool

Condo de Paradise/Salt Water Pool/Boat Dock
LocationFamilyLong stay

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
ValueLocationGrill

Grand Marina Suite - Poolside & Waterfront Condo
LocationFamilyShared spaces

Tropical Escape at Sunrise
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EYW Getaway
LocationFamilyWalkability

Key Wes't Best- Upgraded condo 5 mins to Smathers
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Fully renovated 2/2 bath condo w/ shared pool!
LocationFamilyIndoor spaces

Coral Palms 1BR/King/Queen, Pool, block to Duval
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Other holiday rentals with a pool

Keys Island Villa - Venture Out Home 354
LocationFamilyOutdoor spaces

Sentient Waters: 63’ Boat, Free Snorkel Gear, etc.
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Waterfront Boat Stay + Resort Amenities
ValueLocationComfort

3BR In Resort Village, Pools, Free Kayak & Shuttle
FamilyLocationOutdoor spaces

Newly Renovated 2/2 Bath Condo, with shared pool
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Strictly Pleasure | Unique Yacht Stay in the Keys
LocationFamilyKitchen

Oceanview condo w/pool, jacuzzi and tennis court
LocationFamilyHospitality

Oceanside home 109, dock,kayaks,bikes,pool,fishing
LocationFamilyOutdoor spaces
Destinations to explore
- House rentals Sunset Key
- Rentals with a hot tub Sunset Key
- Waterfront rentals Sunset Key
- Cottage rentals Sunset Key
- Beachfront rentals Sunset Key
- Pet-friendly rentals Sunset Key
- Family-friendly rentals Sunset Key
- Rentals with beach access Sunset Key
- Apartment rentals Sunset Key
- Rentals with pools Key West
- Rentals with pools Monroe County
- Rentals with pools Florida
- Rentals with pools United States
- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Southernmost Point
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium
- Key West Butterfly & Nature Conservatory





