Holiday rentals with a hot tub in Key West

4.89 out of 5 average rating, 177 reviews

An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

Cottage in Cudjoe Key

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!

Outdoor spacesHot tubLocation

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.

4.95 out of 5 average rating, 210 reviews

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

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig & drip coffee New stainless appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, Beach, beach towels One parking space, no charge

BathroomHot tubValue

Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.

4.99 out of 5 average rating, 140 reviews

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.

Outdoor spacesHot tubCondition

4.84 out of 5 average rating, 146 reviews

A refreshing pool area is surrounded by green palm trees and blue umbrellas. Lounge chairs are arranged neatly around the pool, while tables with chairs provide seating for guests. The clear blue sky enhances the inviting atmosphere of the community space.

Apartment in Key West

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.

Outdoor spacesHot tubTV

An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

4.96 out of 5 average rating, 207 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.

Outdoor spacesBathroomLong stay

4.88 out of 5 average rating, 121 reviews

A private outdoor area features a hot tub surrounded by tropical foliage. A dining table with chairs is situated nearby on a wooden deck, offering shade from the overhead structure and a relaxing atmosphere for outdoor meals.

Home in Key West

Near Duval: Hot Tub, Sleeps 6, Top Location

Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

Hot tubOutdoor spacesWalkability

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

4.83 out of 5 average rating, 111 reviews

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.

Outdoor spacesHot tubAccess

A charming entrance is framed by lush tropical plants and palm trees. The light green door complements the inviting beige exterior of the home. A cozy seating area is situated on the porch, and brick pathways lead through a landscaped yard filled with vibrant foliage.

4.94 out of 5 average rating, 124 reviews

Tropical Heron Hideaway w/ Hot Tub + Pool

Welcome to our charming 1932 Key West retreat in the peaceful Meadows neighborhood. This unique getaway features a private porch, a private hot tub, access to a shared pool and BBQ grill, and all the comforts of home. Blending historic island charm with modern amenities, it’s just minutes from Duval Street, the Historic Seaport, beaches, restaurants, and local attractions—the perfect place to relax and experience authentic Key West.

Outdoor spacesHot tubIndoor spaces

A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.

4.87 out of 5 average rating, 135 reviews

*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.

BathroomOutdoor spacesGetting around

4.95 out of 5 average rating, 108 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)

BathroomOutdoor spacesAmenities

4.92 out of 5 average rating, 328 reviews

Home in Key West

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 75” Smart TV. Bose blue tooth speakers and Alexa's. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 6 person Jacuzzi. 2 heated pools!

BathroomOutdoor spacesAir conditioning

4.89 out of 5 average rating, 117 reviews

A bright living area features light-colored furniture, including a comfortable sofa and armchair. A wooden coffee table is centrally placed. Art displays adorn the walls, enhancing the inviting ambiance. Nearby seating accommodates dining for four, with large windows allowing natural light to flow in.

Apartment in Key West

Castaway Cove: Pet-friendly 2/2 condo near beach!

Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.

Hot tubBathroomHospitality

Popular amenities for Key West hot tub accommodation

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a hot tub

A two-story waterfront home is situated under a clear blue sky, surrounded by palm trees and lush greenery. The property features a bright white exterior with a balcony, along with a manicured yard of decorative rocks and native plants.

4.94 out of 5 average rating, 90 reviews

Keys Island Villa - Venture Out Home 354

Hot tubBathroomDecor

A luxury home is set along a serene waterfront, featuring a multi-level design with expansive windows. The property includes a private pool and is surrounded by lush landscaping. A wooden dock extends into the water, providing easy access for water activities.

5 out of 5 average rating, 29 reviews

Luxury 5Bdrm/6bath New in 2024

Hot tubBathroomBackyard

5 out of 5 average rating, 10 reviews

Beach House in Marathon with Amazing Backyard!

Outdoor spacesBathroomAccess

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5 out of 5 average rating, 79 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Hot tubBathroomFamily

5 out of 5 average rating, 12 reviews

P01 - New 3 bed, 3 bath with private pool

Hot tubOutdoor spacesBeach

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

4.81 out of 5 average rating, 321 reviews

AUG/SEPT. Save$ Oceanfront 4 BIKE/2 Kayak KING Bed

BathroomHot tubAccuracy

A bright living area features a green sofa adorned with decorative cushions, flanked by two woven ottomans. Natural light filters through the white curtains, while a large television and colorful wall art enhance the space. Rattan accents and indoor plants bring a refreshing touch.

4.92 out of 5 average rating, 119 reviews

Betty's Place

BathroomHot tubWalkability

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

4.89 out of 5 average rating, 157 reviews

Waterfront Sanctuary in the Keys!

Hot tubBathroomTV

Villa rentals with a hot tub

Villa in Duck Key

Florida Keys 3BR w/ Perks – No Hidden Fees

CheckoutAccuracyHospitality

A covered balcony features two bright blue chairs and a small table. The area offers unobstructed views of the water and surrounding landscape. Sunshine reflects off the surface, highlighting the serene setting.

Villa in Duck Key

2BR Villa in Duck Key | Dolphin Encounters + Pools

Getting aroundViewHospitality

4.91 out of 5 average rating, 77 reviews

A charming two-story villa is framed by swaying palm trees against a bright blue sky. Lush greenery borders the pathway leading to the entrance, which features a porch with round windows and white railings, emphasizing the inviting exterior of the residence.

Villa in Marathon

Seas the Keys Getaway with plunge pool/spa

Outdoor spacesBathroomQuiet

4.78 out of 5 average rating, 9 reviews

Villa in Marathon

Saltwater Social ~ Game Room ~ Pool ~ Dock ~ Views

BathroomOutdoor spacesAccuracy

Villa in Duck Key

Spacious 3BR Villa in Duck Key | Fishing + Pools

HospitalityFamily

Villa in Key Colony Beach

4.98 out of 5 average rating, 46 reviews

Canal/Dock - Cabana Club - Pickleball - Remodeled

Outdoor spacesBathroomValue

4.84 out of 5 average rating, 143 reviews

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.

Villa in Marathon

Villa in Paradise. Plunge pool. Middle of the Keys

BathroomHot tubNearby

4.97 out of 5 average rating, 35 reviews

A coastal-style home features a light green exterior with a covered porch and white railings. Colorful chairs are arranged on the lower deck, while stairs lead up to the entrance. The property is adjacent to a calm waterway, enhancing its scenic appeal.

Villa in Cudjoe Key

Howard House on the Sea

BathroomOutdoor spacesBiking

Other holiday rentals with a spa

5 out of 5 average rating, 26 reviews

Villa Serenity At Sombrero Private Pool Spa Dock

Outdoor spacesBathroomQuiet

4.99 out of 5 average rating, 84 reviews

A modern living area is presented with a comfortable grey sofa and two patterned chairs facing a large sliding door. Natural light fills the space, illuminating a textured wood coffee table and a side table with a lamp. A mounted television displays vibrant sunset imagery.

Apartment in Key West

Newly Renovated 2/2 Bath Condo, with shared pool

Outdoor spacesHot tubPool

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

4.91 out of 5 average rating, 182 reviews

Tropical Escape at Sunrise

BathroomHot tubLocation

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 315 reviews

Affordable Beachfront Luxury Condo Sleeps 6

Hot tubBathroomIndoor spaces

4.87 out of 5 average rating, 260 reviews

A tranquil outdoor pool is surrounded by palm trees, with lounge chairs and tables positioned for relaxation. Umbrellas provide shade near the water, while a charming cottage can be seen in the background under a clear blue sky.

Townhouse in Key West

Poolside Cottage #412

BathroomOutdoor spacesLong stay

Townhouse in Key Colony Beach

A serene outdoor space features two wooden lounge chairs positioned on a grassy area beside calm waters. A small table is placed nearby, and a private dock extends towards the water, flanked by lush greenery in the background under a bright blue sky.

5 out of 5 average rating, 15 reviews

Castillo Del Mar- Ocean access from your backyard

Outdoor spacesParksHospitality

A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

4.99 out of 5 average rating, 85 reviews

EYW Getaway

BathroomLocationComfort

A spacious balcony features two comfortable blue chairs and a small table. The view overlooks lush gardens and the Atlantic Ocean, framed by palm trees. Large sliding glass doors allow access to the interior, while the cloudy sky creates a serene ambiance.