Stock Island vacation rentals

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Popular amenities for Stock Island vacation rentals

Stay near Stock Island's top sights

Hogfish Bar & Grill87 locals recommend
Roostica39 locals recommend
Hurricane Hole28 locals recommend
Publix Super Market at Searstown Shopping Center19 locals recommend
Tavern N' Town12 locals recommend
Lazy Dog Adventures11 locals recommend

Other great vacation rentals in Stock Island

Guest favorite
Apartment in Key West
5 out of 5 average rating, 6 reviews

Casa Caribe 2bed2bath sleeps 6 beautiful decorated

Norma (Jezrael)Rating, 5 stars1 month ago
Judy’s place was one of my favorite we’ve stayed at. She was extremely responsive and helpful. She went above and beyond to accommodate us and we couldn’t be more grateful. Thank you for making our trip so wonderful Judy!
Superhost
Home in Cudjoe Key
4.91 out of 5 average rating, 110 reviews

Sunrise Beach Escape

KimberlyRating, 5 stars1 month ago
The place was really nice. One thing that I didn't like was that the beach really wasn't a beach and to get to the water there was just a little walkway and trying to get the kayak down to the water it was a little hard. The pool needs more lights, so it is easier to see. Also, we had a really hard time with the TV's getting them to work. The king size bed was really comfortable. There were lots to see and do and the place really wasn't too far from Key West so not a bad drive.
Superhost
Home in Marathon
4.62 out of 5 average rating, 26 reviews

Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach

LoriRating, 5 stars37 months ago
Beautiful home that comfortably held our 6 person family of adults. Absolutely loved the pool, spa, and outdoor seating. Really nice kitchen and bathrooms. We used Marathon as home base and drove to Key Largo, Key West, etc. Always nice to return to the house and pool to relax!
Guest favorite
Villa in Marathon
4.95 out of 5 average rating, 135 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

GregRating, 5 stars5 days ago
This was the perfect space for our family of seven. Cleanliness and all the creature comforts were fully up to our expectations. The interactions we had with Dennis were quick, attentive and friendly. Highly recommend!
Top guest favorite
Home in Marathon
4.91 out of 5 average rating, 176 reviews

Beachfront Villa - Florida Keys

ErinRating, 5 stars1 week ago
This is a fantastic property! Right across from Sombrero Beach but still peaceful and private. The house and yard is like an oasis. Host and management company are WONDERFUL! Highly recommend!
Superhost
Home in Marathon
4.6 out of 5 average rating, 5 reviews

Coastal Paradise: 5-Bed Retreat

TrishRating, 5 stars2 weeks ago
We loved our latest stay in Marathon. We traveled with two families (2 teens, 2 older children). The house layout was perfect for our group. It was nice to have the kitchenette downstairs by the patio slider for pool snacks (small microwave) and clean-up from beach days/pool days. The beds were all newer, stylist beach decor, & ample space. There is lots of indoor and outdoor (covered and uncovered) table/conversation seating. The pool and hot tub were great. We spent many nights in the hot tub looking at the stars and relaxing. Although, you on a canal with other houses, it’s very quiet. The canal had fish, sharks, and even a cute manatee that visited in the morning. Our kids loved fishing daily. As for location, it’s perfect. You’re only a few miles from Sombero Beach, Sunset Beach, and 7 mile bridge. Publix, bait shops, restaurants all within a short drive. You cannot walk to beaches, but we didn’t mind this. There is a bike trail on Aviation Rd. Near the house.
Superhost
Home in Marathon
4.75 out of 5 average rating, 4 reviews

SeaEsta! Bring your boat & 1 block to the beach!

KellyRating, 5 stars1 month ago
Our stay at John's place was amazing. The location was perfect as we went up and down the Keys spending time in Islamorada and a day in Key West. We walked the neighborhood and to Sombrero Beach. The set up for our boat was fabulous. We were able to leave it in the water to use everyday. The best part of John's house was the outdoor area in back. We stayed out there more than anywhere, of course the weather was perfect. Thank you for sharing your place with us John. We hope to be back!
Guest favorite
Home in Key Colony Beach
5 out of 5 average rating, 10 reviews

Sleeps 8, 3 bedroom, 4 full bath, pool, 37.5' dock

JeffreyRating, 5 stars7 months ago
Excellent location in a quiet upscale neighborhood. The house was like new, everything was clean and fresh. Very well equipped kitchen and baths. Lots of space indoors and out, with a beautiful small pool! Would definitely recommend this property for a peaceful getaway in the heart of the Florida Keys!!!

Quick stats about vacation rentals in Stock Island

  • Total rentals

    380 properties

  • Nightly prices starting at

    $90 before taxes and fees

  • Total number of reviews

    14K reviews

  • Family-friendly rentals

    280 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    320 properties have a pool

Frequently Asked Questions

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

    Yes! Work meets play with ease at over 210 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 120 vacation rentals for guests traveling with pets.

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

    Experience the best of Stock Island with our resort rentals, starting at about $310 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Stock Island vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 320 vacation homes with pools in Stock Island, available on Airbnb. Make a splash and soak up the sun in style!

  • Do boutique hotel rentals in Stock Island have wifi?

    Absolutely! We offer over 10 boutique hotel rentals with wifi in Stock Island. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Stock Island have self check-in?

    Absolutely! We offer over 30 condo rentals with self check-in in Stock Island. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Stock Island have a bbq area?

    Absolutely! We offer over 10 condo rentals with a bbq area in Stock Island. Enjoy a tailored experience with all the comforts you desire.

  • Do resort rentals in Stock Island have a gym?

    Absolutely! We offer over 10 resort rentals with a gym in Stock Island. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly resort rentals in Stock Island?

    Stock Island has more than 10 family-friendly resort rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 50 homes with wifi, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Stock Island