Villa vacation rentals in Stock Island

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Popular amenities for Stock Island villa rentals

Private villa rentals

Guest favorite
Villa in Marathon
5 out of 5 average rating, 10 reviews

Harbor hideaway 50’dock 3Br/2Ba All amenities

TimRating, 5 stars3 months ago
Loved our stay here! Very private pool and the tiki bar/outside ice maker, was amazing. The house was clean and comfortable with the most comfortable beds ever! The only down side was the location for boating. The dock was excellent and the trip to the 7 mile bridge to fish was conveniently close, however, to do any ocean boating or fishing, the distance thru the sailboat/houseboat harbor was long and we encountered some not so friendly types through there. Over all, to stay and enjoy the privacy of the canal and pool, this was top notch!!!
Top guest favorite
Villa in Duck Key
5 out of 5 average rating, 72 reviews

Duck Key *Bliss* Private Pool & Patio

JamieRating, 5 stars1 month ago
We enjoyed all the little extra touches around the house also loved the privacy of the back yard with the pool.We would definitely stay here again
Top guest favorite
Villa in Marathon
4.95 out of 5 average rating, 138 reviews

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

IngridRating, 5 stars2 weeks ago
Our family of five adults, plus two additional relatives, had the most incredible stay at this property. While we had planned several excursions, we found ourselves spending the majority of our seven-day trip enjoying everything this place had to offer. From fishing off the dock to kayaking and paddleboarding, the outdoor amenities were top-notch. The pool area was the perfect spot for relaxing and spending quality time together. One of the standout features was the amazing outdoor freezer—ideal for storing our fresh catch of Mahi from our charter trip. Inside, the kitchen was impressively well-equipped, making cooking a breeze. Every detail of the home was thoughtfully curated to provide comfort and convenience. This stay exceeded our expectations, and we’re already looking forward to returning. Highly recommend for anyone seeking a well-appointed, adventure-filled getaway!
Top guest favorite
Villa in Key Colony Beach
5 out of 5 average rating, 31 reviews

Canal/Dock - Cabana Club - Pickleball - Remodeled

ErinRating, 5 stars1 week ago
Brian’s place was exceptionally clean. We slept great in the beds. Shower pressure was great. We enjoyed cooking on the grill. Kids enjoyed watching Netflix. Saw a manatee in the canal, that was cool. Great location. Felt very safe walking in the neighborhood. Adored the staff at the Cabana club and the great food and service there. Pool was very clean and great to be right on ocean. Cannot fault this rental in any way. Also Brian checked in with us which was a personal touch that was appreciated. Awesome place!!
Superhost
Villa in Key West
4.62 out of 5 average rating, 45 reviews

Coral Villa by AvantStay| Close 2 DT Key West!

MaryRating, 5 stars3 weeks ago
We had great stay! If we come back to Key West, we will definitely stay here again. The Avant team was highly responsive and great to work with. Check in and check out was extremely easy.
Guest favorite
Villa in Duck Key
4.95 out of 5 average rating, 139 reviews

Beach House - Kayaks & 2/2.5 Villa

JenRating, 5 stars2 weeks ago
This rental was perfect. There is a reason it is rated so well. Every detail is attended to, there are thoughtful touches throughout. We loved the kayaks, walked to Duck Key marina and rented a boat for the day. It’s only a short drive to Key West. The pictures look exactly like what you see when you get there. We thoroughly enjoyed our stay, the accommodations and location are outstanding.
Guest favorite
Villa in Marathon
4.91 out of 5 average rating, 320 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

RobertRating, 5 stars4 days ago
we had a very good experience. everything went well dealing with host. very easy to check I'm, great response time, excellent living quarters. I highly recommend
Guest favorite
Villa in Key West
4.94 out of 5 average rating, 34 reviews

Coral Palm by AvantStay | Mins From DT Key West

MaryRating, 5 stars3 weeks ago
We had great stay! If we come back to Key West, we will definitely stay here again. The Avant team was highly responsive and great to work with. Check in and check out was extremely easy.

Luxury villa rentals

Villa in Duck Key
4.38 out of 5 average rating, 21 reviews

2BR water view with private pool, balcony & kayak

StefanieRating, 5 stars3 months ago
We overall had an amazing stay! Beautiful views, clean house, & responsive hosts!
Villa in Marathon
4.67 out of 5 average rating, 3 reviews

Villa Sombrero

NikkiRating, 5 stars30 months ago
We had a wonderful time. The neighborhood is beautiful, super quiet and nice to walk around. We used the provided paddle boards to go to nearby Sombrero Beach which was lovely. We also walked to Publix and Walgreens. The house itself is really two houses - one upstairs and one downstairs - each with their own kitchens, bedrooms and bathrooms. The house itself is simple and utilitarian, but backyard area is really spectacular. We spent the vast majority of our time outside lounging, playing tennis or swimming in the pool. The location also makes for an easy day trip to Key West. The property manager Jesús was extremely responsive and took care of everything we needed.
Top guest favorite
Villa in Marathon
5 out of 5 average rating, 22 reviews

Indigo Reef water view Villa- #1 Guest Favorite

MarthaRating, 5 stars3 weeks ago
Perfect location in the Middle Keys with easy access to all that Marathon has to offer, Key West or Islamadora. The home is well appointed and the views of the Gulf out the two back porches are spectacular! Very peaceful setting and close to the docks and pool. Would stay here again in a heartbeat!
Superhost
Villa in Duck Key
4.83 out of 5 average rating, 78 reviews

Villa 5034 on Duck Key BOAT SLIP available

MeganRating, 5 stars2 months ago
Frank's place was just as listing shows! Perfect location on Duck Key. Beautiful sunsets right on Tom's Harbour. Would recommend to others!
Top guest favorite
Villa in Duck Key
5 out of 5 average rating, 72 reviews

Duck Key *Bliss* Private Pool & Patio

JamieRating, 5 stars1 month ago
We enjoyed all the little extra touches around the house also loved the privacy of the back yard with the pool.We would definitely stay here again
Guest favorite
Villa in Marathon
5 out of 5 average rating, 10 reviews

Waterfront Villa (38) w/ sunset views & boat slip

KatrinRating, 5 stars2 months ago
Great location on the property. Beautiful view of the water and the pool. Nice big porch to relax on with plenty of chairs. Provided plenty of towels and the kitchen had everything you needed. Could have used more TB, PT and some dishwasher soap but all good. This place is a favorite of ours to just relax and go boating! Highly recommend!!
Superhost
Villa in Key West
4.62 out of 5 average rating, 45 reviews

Coral Villa by AvantStay| Close 2 DT Key West!

MaryRating, 5 stars3 weeks ago
We had great stay! If we come back to Key West, we will definitely stay here again. The Avant team was highly responsive and great to work with. Check in and check out was extremely easy.
Villa in Marathon

"Keepin’ It Reel" Waterfront, 4BD/3BA FL Keys Home

DanteRating, 5 stars3 months ago
The home and the location and the dock are all fantastic. The home is at the end of the channel so it takes a bit to get to, but you also don't have traffic so your boat is secure and not subject to other wakes, and there were a lot of iguanas which was really cool! The home is very well appointed and luxurious and also close to the main road so its easy to get to Publix and local restaurants. It also has all the pots and pans you could need. The master bedroom is spacious and has a nice bathroom and the sunset from the master is incredible. I highly recommend this property, 10/10 would absolutely rent it again! The ice machine was a really nice touch, it gave me enough ice for the cooler and the boat cooler every morning! Access to the Atlantic via boat takes about 20 minute and access to the Gulf via boat takes about 25 minutes.

Villa rentals with a pool

Guest favorite
Villa in Marathon
5 out of 5 average rating, 10 reviews

Harbor hideaway 50’dock 3Br/2Ba All amenities

TimRating, 5 stars3 months ago
Loved our stay here! Very private pool and the tiki bar/outside ice maker, was amazing. The house was clean and comfortable with the most comfortable beds ever! The only down side was the location for boating. The dock was excellent and the trip to the 7 mile bridge to fish was conveniently close, however, to do any ocean boating or fishing, the distance thru the sailboat/houseboat harbor was long and we encountered some not so friendly types through there. Over all, to stay and enjoy the privacy of the canal and pool, this was top notch!!!
Villa in Duck Key
5 out of 5 average rating, 3 reviews

Florida Keys Sanctuary

VictoriaRating, 5 stars2 weeks ago
I celebrated both my mom’s birthday and mine here, and from the moment I booked until check-out, the experience was nothing short of amazing. The property manager was incredibly helpful, responsive, and made everything seamless. Highly recommend!
Villa in Marathon

Luxury Waterfront Villa, Marathon, Florida Keys

ShawnRating, 5 stars5 months ago
Very clean quiet and an excellent pool area!
Top guest favorite
Villa in Marathon
4.95 out of 5 average rating, 138 reviews

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

IngridRating, 5 stars2 weeks ago
Our family of five adults, plus two additional relatives, had the most incredible stay at this property. While we had planned several excursions, we found ourselves spending the majority of our seven-day trip enjoying everything this place had to offer. From fishing off the dock to kayaking and paddleboarding, the outdoor amenities were top-notch. The pool area was the perfect spot for relaxing and spending quality time together. One of the standout features was the amazing outdoor freezer—ideal for storing our fresh catch of Mahi from our charter trip. Inside, the kitchen was impressively well-equipped, making cooking a breeze. Every detail of the home was thoughtfully curated to provide comfort and convenience. This stay exceeded our expectations, and we’re already looking forward to returning. Highly recommend for anyone seeking a well-appointed, adventure-filled getaway!
Superhost
Villa in Marathon

Refreshed & Elevated Indigo Reef Luxury Villa 15,

HenryRating, 5 stars14 months ago
Beautiful location in the Keys. We loved our stay, and the unit was comfortable, clean and new. Great pool, wonderful dock and pleasant neighbors. Would definitely come back!
Top guest favorite
Villa in Key Colony Beach
5 out of 5 average rating, 31 reviews

Canal/Dock - Cabana Club - Pickleball - Remodeled

ErinRating, 5 stars1 week ago
Brian’s place was exceptionally clean. We slept great in the beds. Shower pressure was great. We enjoyed cooking on the grill. Kids enjoyed watching Netflix. Saw a manatee in the canal, that was cool. Great location. Felt very safe walking in the neighborhood. Adored the staff at the Cabana club and the great food and service there. Pool was very clean and great to be right on ocean. Cannot fault this rental in any way. Also Brian checked in with us which was a personal touch that was appreciated. Awesome place!!
Superhost
Villa in Key West
4.62 out of 5 average rating, 45 reviews

Coral Villa by AvantStay| Close 2 DT Key West!

MaryRating, 5 stars3 weeks ago
We had great stay! If we come back to Key West, we will definitely stay here again. The Avant team was highly responsive and great to work with. Check in and check out was extremely easy.
Guest favorite
Villa in Marathon
4.91 out of 5 average rating, 320 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

RobertRating, 5 stars4 days ago
we had a very good experience. everything went well dealing with host. very easy to check I'm, great response time, excellent living quarters. I highly recommend

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