Stock Island vacation rentals

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Top-rated vacation rentals in Stock Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Bungalow in Key West

4.93 out of 5 average rating, 104 reviews

Atlantis House's Banyan Suite-voted top 25 in USA

About this space Atlantis House with just two exclusive rooms, the Master suite and the Garden suite, is the most private and romantic guesthouse in Key West. Rated a 2021 Travelers’ Choice Award by Trip Advisor. Perfect for Honeymoons and Anniversaries. A "little jewel" tucked away inside a lush tropical garden just steps away from the beaches. NOTE: Superhost Shari is a new owner of this property. Past reviews do not transfer but are 5-STAR! This suite The Banyan Suite (previously called Garden Suite) is nestled in the corner of the lush backyard with a private French door entrance off the deck. This charming hideaway offers a large flat screen TV visible from the sofa and spacious king bed. Relax to island music on the Bose Mini Bluetooth speaker while you power up devices on provided chargers for countless photo op filled adventures that await! A corner bar table provides the perfect spot to enjoy a quick bite from the quaint kitchenette equipped with a mini-fridge, microwave oven, toaster, and coffeemaker, featuring famous Cuban coffee! Rejuvenate in the coveted in-room whirlpool bath with bubbles and soaking salts or cool off in the open shower with bench seating. The vanity is stocked with many toiletries and our white all-cotton bath robes allow for an extended spa experience. Please Note: The Banyan Suite is one of only two guest suites, separate from the Main Residence. The two suites have exclusive use of the lush backyard oasis with tropical trees, plenty of seating areas to enjoy the natural sounds of local wildlife or the pages of a good book. There is also a shared propane BBQ on the deck and an additional refrigerator with extra storage & ice located next to the complimentary cruiser bikes! The Banyan and Palm Suites each accommodate a maximum of 2 adults – Special accommodation for children may be included if the two guest suites are booked together. Guest access Guests have their own private entrance. Past reviews 5.0 out of 5 stars Cleanliness 5.0 Accuracy 5.0 Communication 5.0 Location 5.0 Check-in 5.0 Value 5.0

Feb 4 – 11

$774 per night

Guest favorite

Home in Key West

4.94 out of 5 average rating, 270 reviews

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

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Jul 1 – 8

$465 per night

Guest favorite

Townhouse in Key West

4.89 out of 5 average rating, 104 reviews

Charming Key West Vacation Rental 3bedrm/3bath

Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available. Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler items available upon request. Portable Crib, high chair & more.

Jun 28 – Jul 5

$525 per night

Guest favorite

Townhouse in Key West

4.87 out of 5 average rating, 174 reviews

*Sparkling new kitchen* 3 bedroom/3 bath home.

Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and two queen beds. The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer installed. The salt water pool is perfect for lazing away your days. There is on street parking for two cars. The center of town is ten minutes away. An entire home for the price of one hotel room.

Sep 23 – 30

$406 per night

Superhost

Houseboat in Key West

4.81 out of 5 average rating, 253 reviews

Key West Houseboat Paradise

56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats. The property has an fairly industrial feel to it with a 2-bay local garage/taxi company on site so Shore Side is nuthin' fancy but the back deck looks out on mangrove islands dotting Boca Chica Channel with two 12' Sea Kayaks ready to go.

Nov 8 – 15

$344 per night

Superhost

Vacation home in Key West

4.88 out of 5 average rating, 226 reviews

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.

Mar 6 – 13

$354 per night

Superhost

Houseboat in Key West

4.84 out of 5 average rating, 174 reviews

Happys Houseboat

This beautiful houseboat is nestled in a calm protected bay, it has hot water, a fridge and Air Conditioning! This boat was featured in Old Dominion‘s music video “I was on a boat that day”. Beautiful sites all around to wake up on the water and sunsets and stars to experiences as you relax on the top deck in the evening. Included in the rental is use of a skiff to get to and from land and and a seventh generation local captain to assist in check in and give a tour of the Houseboat.

Aug 4 – 11

$333 per night

Guest favorite

Guesthouse in Key West

4.93 out of 5 average rating, 526 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.

Jun 23 – 30

$319 per night

Guest favorite

Condo in Key West

4.88 out of 5 average rating, 144 reviews

Large waterfront 2/2 end unit with boat slip

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grills, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Nov 11 – 18

$621 per night

Guest favorite

Townhouse in Key West

4.91 out of 5 average rating, 109 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Dec 16 – 23

$373 per night

Superhost

Apartment in Key West

4.89 out of 5 average rating, 908 reviews

At Mine | Key West 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.

Aug 16 – 23

$219 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Stock Island vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Stock Island's top sights

Boyd's Key West Campground6 locals recommend

Lazy Dog Adventures11 locals recommend

Hogfish Bar & Grill87 locals recommend

Hurricane Hole28 locals recommend

Roostica39 locals recommend

Chico's Cantina10 locals recommend

Other great vacation rentals in Stock Island

Superhost

Boat in Key West

4.79 out of 5 average rating, 71 reviews

The Escape- Private 2 Bed Rm Boat Beautiful Marina

Jul 13 – 20

$235 per night

Guest favorite

Boat in Key West

4.93 out of 5 average rating, 40 reviews

Sailboat in Luxury Marina

Jul 9 – 16

$225 per night

Guest favorite

Townhouse in Key West

4.94 out of 5 average rating, 16 reviews

Casa Coral

Jun 2 – 9

$382 per night

Guest favorite

Condo in Key West

5.0 out of 5 average rating, 24 reviews

Gorgeous Ocean View in Paradise

Aug 20 – 27

$387 per night

Guest favorite

Apartment in Stock Island

4.84 out of 5 average rating, 19 reviews

"Hemingway" 1 bedroom at Leo's

Aug 6 – 13

$239 per night

Guest favorite

Home in Key West

4.98 out of 5 average rating, 43 reviews

Gone Coastal

Aug 19 – 26

$342 per night

Guest favorite

Home in Key West

5.0 out of 5 average rating, 63 reviews

Clean and Relaxing! 3 King Suites! With everything

Jun 12 – 19

$675 per night

Guest favorite

Condo in Key West

4.93 out of 5 average rating, 14 reviews

Top Floor Pool View Suite with Rooftop Balcony

Aug 20 – 27

$414 per night

Show all

Other great vacation rentals in Stock Island

Guest favorite

Condo in Key West

4.96 out of 5 average rating, 84 reviews

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

Jun 10 – 17

$424 per night

Guest favorite

Condo in Key West

4.96 out of 5 average rating, 76 reviews

Hidden Beach unit 1 The Perfect Place to stay

Nov 25 – Dec 2

$536 per night

Superhost

Condo in Key West

4.91 out of 5 average rating, 96 reviews

Tropical Escape at Sunrise

Sep 20 – 27

$329 per night

Superhost

Cottage in Key West

4.95 out of 5 average rating, 84 reviews

Mango Cottage 2 bedroom 2 bath with private pool

Aug 14 – 21

$445 per night

Guest favorite

Houseboat in Key West

4.82 out of 5 average rating, 11 reviews

The simple life on Seaplicity!

Dec 23 – 30

$251 per night

Superhost

Houseboat in Key West

4.92 out of 5 average rating, 39 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

Feb 11 – 18

$455 per night

Superhost

Boat in Key West

4.91 out of 5 average rating, 11 reviews

Amazing 4 Bdrm, 4 Bath Catamaran - Purpus

Jul 2 – 9

$809 per night

Guest favorite

Apartment in Key West

4.93 out of 5 average rating, 15 reviews

Oceanfront Condo in Key West

Dec 13 – 20

$606 per night

Show all

Quick stats about vacation rentals in Stock Island

Total rentals
110 properties
Rentals with a pool
70 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
5.4K reviews
Nightly prices starting at
$90 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Stock Island?
Yes! Work meets play with ease at over 50 vacation rentals in Stock Island featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Stock Island?
Four-legged friends are welcome in Stock Island. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there Stock Island townhouse rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 townhouse rentals with pools in Stock Island, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Stock Island have wifi?
Absolutely! We offer over 20 house rentals with wifi in Stock Island. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Stock Island have air conditioning?
Absolutely! We offer over 10 townhouse rentals with air conditioning in Stock Island. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in townhouse rentals in Stock Island?
Experience the best of Stock Island with our townhouse rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly boat rentals in Stock Island?
Stock Island has more than 30 family-friendly boat rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Stock Island have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Stock Island. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Stock Island have a gym?
Absolutely! We offer over 10 townhouse rentals with a gym in Stock Island. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Boat Rentals in Stock Island?
Enhance your stay in our Boat Rentals with the most popular amenities: over 20 homes with a gym, over 40 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Stock Island vacation rentals

Top-rated vacation rentals in Stock Island

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Stock Island vacation rentals

Stay near Stock Island's top sights

Other great vacation rentals in Stock Island

Boat in Key West

Boat in Key West

Townhouse in Key West

Condo in Key West

Apartment in Stock Island

Home in Key West

Home in Key West

Condo in Key West

Other great vacation rentals in Stock Island

Condo in Key West

Condo in Key West

Condo in Key West

Cottage in Key West

Houseboat in Key West

Houseboat in Key West

Boat in Key West

Apartment in Key West

Quick stats about vacation rentals in Stock Island

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Stock Island?

Are there pet-friendly vacation rentals in Stock Island?

Are there Stock Island townhouse rentals on Airbnb with pools?

Do house rentals in Stock Island have wifi?

Do townhouse rentals in Stock Island have air conditioning?

How much does it cost to stay in townhouse rentals in Stock Island?

Are there family-friendly boat rentals in Stock Island?

Do house rentals in Stock Island have a bbq area?

Do townhouse rentals in Stock Island have a gym?

What are the most popular amenities for Boat Rentals in Stock Island?

Destinations to explore