Gulf Stream Cottage Rentals & Holiday Homes

Find the best cottages in Gulf Stream - We found 59 exact matches

About Gulf Stream Cottage Rentals on PickleTrip

Searching for cottages to rent near Gulf Stream? PickleTrip™ features more than 59 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in Gulf Stream have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Gulf Stream.

Are you planning to travel to the lakeside, beach, or mountain area? PickleTrip™’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

PickleTrip™ boasts of 59 holiday cottages and places to stay in Gulf Stream. The site provides unique Airbnb, VRBO, pickleball-ready cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday — all fitting within your budget.

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Frequently Asked Questions About Gulf Stream Rental Cottages

There are a lot of options in Gulf Stream. If you plan on staying in the Gulf Stream area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Gulf Stream:

The average cost for a cottage rental in Gulf Stream is $294 per night. PickleTrip has a wide list of great cottages near Gulf Stream that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Gulf Stream that allow you to bring your pet:

See all pet-friendly vacation rentals in Gulf Stream on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Gulf Stream to find one that works for you.
As of 2026, the data from PickleTrip shows that there are Over 59 private swimming pools or cottages with indoor pools in the Gulf Stream area along with other great amenities.
About 59 cottages in Gulf Stream boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Gulf Stream on PickleTrip
Yes, there are luxury cottages in Gulf Stream. Find more luxury, lakefront, winter, & last-minute cottage rentals near Gulf Stream.