Winter Haven vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Winter Haven

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

Superhost

Cottage in Winter Haven

4.8 out of 5 average rating, 113 reviews

Just Beachin' Cabin Unit 10

Experience the tranquility of the Sunshine State from this quaint-yet-modern vacation rental home, complete with 2 bedrooms, 2 bathrooms, a private deck, and modern interior finishes. You’ll enjoy direct access to a boat launch and the Chain of Lakes, a fishing and boating paradise complete with 24 canal-connected lakes! Spend your days out on the water, make incredible memories with your family at LEGOLAND Florida, or opt to visit the theme parks in Orlando - from this home, you can do it all!

Oct 1 – 8

G$27,291 GYD per night
Guest favorite

Guesthouse in Winter Haven

4.94 out of 5 average rating, 198 reviews

The Paradise Hide Away

This is a beautiful and private place newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! Talk to me if you need different check in/out times? Dogs are allowed with permission. There is a $200 fully refundable pet security deposit to cover any damages that may occur since Airbnb doesn’t cover damages caused by pets plus a non refundable pet fee of $50 per pet for every 1-7 day period and must be paid before checking in !

Aug 25 – Sep 1

G$15,173 GYD per night
Guest favorite

Apartment in Winter Haven

4.99 out of 5 average rating, 135 reviews

Florida Penthouse in luxurious mansion!

Stay in your own themed Florida apartment . Tropical, palm trees, beaches ,marine life, flamingos throughout this stunning apartment in a multimillion dollar home. After parking on gated driveway walk up to your own private entrance way to paradise. Keyless entrance. One flight up and your viewing gorgeous lake views second to none. Executive kitchen with everything you need to cook a 5 course meal. Outdoor balcony that will leave you amazed. Opulence, security, with Florida Style awaits you!

Apr 28 – May 5

G$21,550 GYD per night

Popular amenities for Winter Haven vacation rentals

Stay near Winter Haven's top sights

LEGOLAND Florida Water Park104 locals recommend
Winter Haven Hospital4 locals recommend
Harborside25 locals recommend
Manny's Chophouse- Winter Haven9 locals recommend
Andy's Dine-In Restaurant14 locals recommend
Azteca D' Oro8 locals recommend

Winter Haven home rentals

Superhost

Home in Winter Haven

4.79 out of 5 average rating, 269 reviews

Florida Oasis w/ Pool near LEGOLAND

Jan 26 – Feb 2

G$29,543 GYD per night
Superhost

Home in Winter Haven

4.86 out of 5 average rating, 189 reviews

💎LakeFront💎ModernCottageTiny-Home☀🎢4milesLEGOLAND🎢

Jul 24 – 31

G$20,193 GYD per night
Superhost

Home in Winter Haven

4.9 out of 5 average rating, 256 reviews

The Old Haven - An Enduring Piece of Nostalgia

Nov 6 – 13

G$30,555 GYD per night
Guest favorite

Home in Haines City

4.88 out of 5 average rating, 136 reviews

3 Bedroom Executive with Private Pool near Disney

Oct 23 – 30

G$27,836 GYD per night
Guest favorite

Home in Winter Haven

4.91 out of 5 average rating, 150 reviews

Hidden Haven Lakehouse Pool by Legoland

Jul 30 – Aug 6

G$41,686 GYD per night
Superhost

Home in Winter Haven

4.83 out of 5 average rating, 127 reviews

Florida Getaway near Legoland& Orlando Attractions

Aug 1 – 8

G$25,541 GYD per night
Guest favorite

Home in Haines City

4.96 out of 5 average rating, 137 reviews

Luxury Home 4/3 near Disney, 2 Masters

Sep 15 – 22

G$32,317 GYD per night
Guest favorite

Home in Winter Haven

4.91 out of 5 average rating, 143 reviews

A Little Slice of "Haven" Home (No Cleaning Fee)

Feb 24 – Mar 3

G$31,072 GYD per night
Guest favorite

Home in Lakeland

4.95 out of 5 average rating, 111 reviews

Cute, Historic District Home - GREAT LOCATION

Jul 6 – 13

G$29,873 GYD per night
Guest favorite

Home in Lakeland

4.91 out of 5 average rating, 376 reviews

Charming guest house

Jul 3 – 10

G$21,638 GYD per night
Guest favorite

Home in Winter Haven

4.88 out of 5 average rating, 33 reviews

Newly remodeled House 3BR/2BA

Dec 7 – 14

G$22,164 GYD per night
Guest favorite

Home in Winter Haven

4.97 out of 5 average rating, 62 reviews

The Dalt Retreat

Jul 30 – Aug 6

G$27,361 GYD per night

Other great vacation rentals in Winter Haven

Guest favorite

Guesthouse in Auburndale

4.97 out of 5 average rating, 191 reviews

Private Poolside Villa

Jul 31 – Aug 7

G$16,675 GYD per night
Guest favorite

Villa in Lake Wales

4.99 out of 5 average rating, 179 reviews

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

Dec 6 – 13

G$32,040 GYD per night
Guest favorite

Apartment in Auburndale

4.96 out of 5 average rating, 211 reviews

Ariana Place - Tree House Like Lakefront Views

Dec 2 – 9

G$18,295 GYD per night
Guest favorite

Guesthouse in Lake Alfred

4.96 out of 5 average rating, 113 reviews

Adorable Agave Suite w/ private pool and entrance

May 5 – 12

G$18,681 GYD per night
Guest favorite

Guesthouse in Winter Haven

4.87 out of 5 average rating, 141 reviews

Brutus Way Cottage, a cosy hide away

Jul 4 – 11

G$17,236 GYD per night
Superhost

Cottage in Davenport

4.92 out of 5 average rating, 123 reviews

$79! Cozy Cottage + Outdoor Fun -Close to Disney!

May 28 – Jun 4

G$19,819 GYD per night
Guest favorite

Loft in Auburndale

4.94 out of 5 average rating, 131 reviews

2 Bedroom Apartment near Legoland and Disney

Aug 11 – 18

G$25,428 GYD per night
Guest favorite

Cabin in Davenport

4.92 out of 5 average rating, 164 reviews

$89! Cozy Cabin- Disney 20 Miles Away!

May 6 – 13

G$22,209 GYD per night
Guest favorite

Guesthouse in Lake Hamilton

4.9 out of 5 average rating, 134 reviews

Luxury Cottage Near Legoland & Chain of Lakes

Aug 31 – Sep 7

G$28,589 GYD per night
Guest favorite

Guesthouse in Winter Haven

4.91 out of 5 average rating, 47 reviews

Comfy Guest House

Nov 20 – 27

G$18,490 GYD per night
Guest favorite

Guesthouse in Auburndale

4.98 out of 5 average rating, 89 reviews

Cozy 2-bedroom guesthouse on the lake

Jan 9 – 16

G$24,095 GYD per night
Guest favorite

Guest suite in Winter Haven

4.86 out of 5 average rating, 71 reviews

Cute & Cozy Guesthouse in Winter Haven

Jun 8 – 15

G$16,942 GYD per night

Quick stats about vacation rentals in Winter Haven

Total rentals

360 properties

Rentals with dedicated workspaces

210 properties have a dedicated workspace

Rentals with a pool

80 properties have a pool

Pet-friendly rentals

120 properties allow pets

Family-friendly rentals

200 properties are a good fit for families

Total number of reviews

13K reviews

Frequently Asked Questions

  • Where should I stay in Winter Haven?

    Make yourself at home in Winter Haven by choosing from our most frequently booked neighborhoods. We have over 240 vacation rentals in Downtown Winter Haven, over 240 vacation rentals in Eagle Lake, and over 240 vacation rentals in Florence Villa.

  • Are there vacation rentals with a dedicated workspace in Winter Haven?

    Yes! Work meets play with ease at over 210 vacation rentals in Winter Haven featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winter Haven?

    Four-legged friends are welcome in Winter Haven. Choose from more than 120 vacation rentals for guests traveling with pets.

  • Are there Winter Haven vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 80 vacation homes with pools in Winter Haven, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in guesthouse rentals in Winter Haven?

    Experience the best of Winter Haven with our guesthouse rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in Winter Haven?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with a bbq area, over 10 homes with a gym, over 80 homes with self check-in, over 250 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Winter Haven?

    Winter Haven has more than 200 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Winter Haven have a bbq area?

    Absolutely! We offer over 50 house rentals with a bbq area in Winter Haven. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Winter Haven have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Winter Haven. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Haven have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Winter Haven. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Polk County
  5. Winter Haven