What are the top rated Cottage Rentals in Lakeland - Winter Haven?

There are a lot of options in Lakeland - Winter Haven. If you plan on staying in the Lakeland - Winter Haven area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Lakeland - Winter Haven: <a href="/property/3-br-villa-large-pool-hot-tub-25-min-to-disney-2-king-size-beds-1-queen/HA-1214023493" class="class="static-page-link"">3 BR VILLA. Large pool. Hot tub. 25 min to Disney. 2 King Size Beds, 1 queen</a> <a href="/property/top-rated-scandinavian-luxury-villa-exclusive-with-private-pool-golf-view/HA-1214258540" class="class="static-page-link"">TOP RATED SCANDINAVIAN LUXURY VILLA - Exclusive with Private Pool &amp; Golf View</a> <a href="/property/beautiful-home-with-white-sand-beach-on-stunning-crooked-lake/HA-3213015922" class="class="static-page-link"">Beautiful home with white sand beach on stunning Crooked Lake</a> <a href="/property/award-winning-golf-disney-universal-pool-clubhouse-gated-community/HA-3212151039" class="class="static-page-link"">☀️🌴Award-Winning Golf, Disney/Universal, Pool, Clubhouse/Gated Community 🌴☀️</a> <a href="/property/lakeland-fl-swan-city-get-away-entire-house/HA-3211775882" class="class="static-page-link"">LAKELAND, FL SWAN CITY GET-AWAY ENTIRE HOUSE</a> <a href="/property/cottage-w-private-pool-walk-to-lake-wales/HA-1217628548" class="class="static-page-link"">Cottage w/Private Pool - Walk to Lake Wales!</a> <a href="/property/stay-in-luxury-private-pool-spa-games-room-close-to-disney-and-golf/HA-1214831050" class="class="static-page-link"">Stay in Luxury, Private Pool/Spa, Games Room, Close to Disney and Golf</a> <a href="/property/waterfront-winter-haven-home-with-dock-hot-tub/HA-1217401677" class="class="static-page-link"">Waterfront Winter Haven Home with Dock &amp; Hot Tub!</a> <a href="/property/lake-house-with-private-free-heated-pool-game-room-4-min-from-legoland/HA-3212730730" class="class="static-page-link"">LAKE HOUSE WITH PRIVATE Free HEATED POOL &amp; GAME ROOM 4 min FROM LEGOLAND</a> <a href="/property/lake-retreat-w-pool-hot-tub-near-bok-tower/HA-3212449946" class="class="static-page-link"">Lake Retreat w/Pool &amp; Hot Tub near Bok Tower</a>

How much does it cost to rent a cottage in Lakeland - Winter Haven?

The average cost for a cottage rental in Lakeland - Winter Haven is $108 per night. Unpluggedweekend has a wide list of great cottages near Lakeland - Winter Haven that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Lakeland - Winter Haven that allow pets?

Yes, here are the top cottage rentals in Lakeland - Winter Haven that allow you to bring your pet: Cozy Oasis-Charming 1 Bedroom Casita with RV Parking Available Gem of Lake Marion! Beautiful 3 Bedroom with King Beds, HD & Internet Southern Dunes Golf & Country Club 215707 Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn 3 BR VILLA. Large pool. Hot tub. 25 min to Disney. 2 King Size Beds, 1 queen <a href="/all/usa/florida/lakeland-winter-haven" class="class="static-page-link"">See all pet-friendly vacation rentals in Lakeland - Winter Haven on Unpluggedweekend</a>

Do you have any rental cottages in Lakeland - Winter Haven that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Lakeland - Winter Haven to find one that works for you.

Are there quality cottages in Lakeland - Winter Haven that have indoor swimming pools?

As of 2026, the data from Unpluggedweekend shows that there are Over 1 private swimming pools or cottages with indoor pools in the Lakeland - Winter Haven area along with other great amenities.

Unpluggedweekend - Lakeland - Winter Haven Cottage Rentals By Owner

Cozy Oasis-Charming 1 Bedroom Casita with RV Parking Available

From US $108

New

Cottage

Cozy Oasis-Charming 1 Bedroom Casita with RV Parking Available

Air Conditioner
Pool
Balcony/Terrace

Lakeland - Winter Haven Cottage Rentals & Holiday Homes

Find the best cottages in Lakeland - Winter Haven - We found 1 exact matches

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