Winter Haven Hotels with Outdoor or Indoor Pools

Quality Inn & Suites Conference Center - Winter Haven
+1-888-389-4121
5665 Cypress Gardens Blvd., Winter Haven, FL 33884 +1-888-389-4121
  • Pool details: 8am-10pm Outdoor oversized pool
  • Economy Lake property
From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
Best Western Plus Winter Haven Inn & Suites 
+1-888-675-2083
5801 Roosevelt Dr., Winter Haven, FL 33884 +1-888-675-2083
  • Pool available: Sparkling outdoor pool open daily 10 AM - 8 PM, weather permitting.
  • Affordable Suburban property
From$49
Average 3.0 /5 Hotel Reviews Call BookMore Details
Staybridge Suites Winter Haven Auburndale in Winter Haven
+1-800-716-8490
305 5th St. Nw, Winter Haven, FL 33881 +1-800-716-8490
  • Has a pool!
  • 3 star hotel
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Best Western Auburndale Inn & Suites
+1-800-805-5223
1008 Us Highway 92 West, Auburndale, FL 33823 +1-800-805-5223 ~5.88 miles west of Winter Haven
  • Has swimming pool: Our outdoor heated pool measures 450 square feet and it is open year around from dawn until dusk.
  • Mid-scale Highway hotel
From$84
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Lake Wales North Winter Haven
+1-888-965-1860
2953 Ridge Way, Lake Wales, FL 33859 +1-888-965-1860 ~7.86 miles southeast of Winter Haven
  • We have a pool
  • Affordable Suburban property
From$109
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn Lakeland
+1-888-788-5576
4420 North Socrum Loop Rd., Lakeland, FL 33809 +1-888-788-5576 ~14.33 miles west of Winter Haven
  • Pool details: Out Door 9 AM-9PM
  • 3 star Suburban property
From$100
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Days Inn & Suites by Wyndham Lakeland : 4502 North Socrum Loop Rd.
+1-888-897-9207
4502 North Socrum Loop Rd., Lakeland, FL 33809 +1-888-897-9207 ~14.33 miles west of Winter Haven
  • Pool in hotel: Outdoor Pool : Pool hours : 8 AM - 8 PM
  • Low-priced Highway property
From$63
Very Good 4.0 /5 Read Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Lakeland East in Lakeland
+1-888-311-4278
4315 Lakeland Park Dr., Lakeland, FL 33809 +1-888-311-4278 ~14.40 miles west of Winter Haven
  • Has a pool!
  • Midscale Highway property
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Lakeland North I 4 in Lakeland
+1-888-469-4795
4500 Lakeland Park Rd., Lakeland, FL 33809 +1-888-469-4795 ~14.42 miles west of Winter Haven
  • Pool available: 6am - 9pm
  • Mid-scale Suburban hotel
From$79
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Howard Johnson by Wyndham Lakeland in Lakeland
+1-888-734-9421
939 West Robson St., Lakeland, FL 33805 +1-888-734-9421 ~14.99 miles west of Winter Haven
  • Pool available: Outdoor pool. Hours: Sunrise to Sunset. 45ft X 27ft.
  • Mid-scale Downtown property
Hampton Inn & Suites Lakeland South Polk Parkway
+1-888-841-5292
3630 Lakeside Village Blvd., Lakeland, FL 33803 +1-888-841-5292 ~15.11 miles west of Winter Haven
  • Has swimming pool: Heated pool is open daily from 6am to 10pm
  • Affordable Suburban hotel
From$89
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Home2 Suites by Hilton Lakeland
+1-888-455-5160
3610 Lakeside Village Boulevar, Lakeland, FL 33142 +1-888-455-5160 ~15.13 miles west of Winter Haven
  • Pool in hotel: Open From 6:00am to 10:00pm and its an outdoor pool .
  • 3 star property
From$50
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Travelodge Lakeland in Lakeland
+1-888-965-8297
3425 Highway 98 North, Lakeland, FL 33809 +1-888-965-8297 ~15.15 miles west of Winter Haven
  • Pool available: 8am to sundown
  • Two-star Highway property
From$50
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Ramada by Wyndham Davenport Orlando South
+1-888-906-6358
43824 Us Highway 27, Davenport, FL 33837 +1-888-906-6358 ~15.26 miles north of Winter Haven
  • Includes a pool: 10AM to 10PM 25000 gallons Outdoor
  • Low priced Highway property
From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
Comfort Inn & Suites Lakeland : 3520 North Highway 98
+1-888-749-6785
3520 North Highway 98, Lakeland, FL 33809 +1-888-749-6785 ~15.30 miles west of Winter Haven
  • Pool in hotel
  • Affordable Highway property
From$81
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Ramada by Wyndham Davenport Orlando South : 43824 Highway 27
+1-888-878-9982
43824 Highway 27, Davenport, FL 33837 +1-888-878-9982 ~15.35 miles north of Winter Haven
  • Pool available: 8 AM to 8PM 25000 gallons Outdoor
  • 2-star Highway hotel
From$33
Poor 2.0 /5 Reviews Call BookMore Details
Villatel Village - Davenport
+1-888-389-4485
1713 Oak Blossom Dr., Davenport, FL 33837 +1-888-389-4485 ~16.48 miles northeast of Winter Haven
  • Includes a pool: Each home has its own private pool.
  • 4 star property
From$300
Average 3.0 /5 Recent Reviews Call BookMore Details
Omni Orlando Resort at Championsgate in Championsgate
+1-888-389-4121
1500 Masters Blvd., Championsgate, FL 33896 +1-888-389-4121 ~17.75 miles north of Winter Haven
  • Has swimming pool: Zero-Entry Family Pool The zero-entry family pool allows guests to skip the stairs and submerge slowly into the pool as they would the ocean. As parents ease into the pool, children have a blast in the nearby liquid playground, cooling off under dancing water fountains and 30-foot spilling water tower. For the ultimate Orlando thrill ride, kids race to the top of the 125-foot corkscrew waterslide, splashing and laughing the whole way down. Lazy River The 850-foot lazy river lets kids of all ages float on bright tubes at speeds ranging from two to eight mph, through its tunnels, gentle rapids and hidden canyons. Winding through the lushly landscaped resort playground, the lazy river channels adventurers through H20 surprises ranging from shooting water cannons to rainbows of arched waterspouts and an exhilarating waterfall. Private Cabanas & Formal Pool Eight private cabanas line the formal pool with opportunity for guests to “own” one for the day. Donning luxurious robes and sipping on fresh fr
  • Four-star Resort hotel
From$119
Average 3.0 /5 Reviews Call BookMore Details
Home2 Suites by Hilton Orlando South Davenport
+1-888-675-2083
164 Thrive Rd., Davenport, IA 33896 +1-888-675-2083 ~17.92 miles north of Winter Haven
  • Pool details: Outdoor Pool
  • High-end Suburban property
From$100
Average 3.0 /5 Reviews Call BookMore Details
Alhambra Villas - Poinciana
+1-800-716-8490
500 Cypress Pkwy., Poinciana, FL 34759 +1-800-716-8490 ~18.37 miles east of Winter Haven
  • Pool available: Outdoor pool
  • 3-star Resort property
From$49
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Reunion Resort & Golf Club
+1-800-805-5223
7593 Gathering Dr., Kissimmee, FL 34747 +1-800-805-5223 ~19.26 miles northeast of Winter Haven
  • Includes a pool: 11 Pools, Vary in Size and Hours. All Outdoors. Water Park on property, lazy river
  • 4 star Resort property
From$309
Average 3.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites by Marriott Lakeland Plant City - Lakeland
+1-888-965-1860
4307 Sterling Commerce Dr., Lakeland, FL 33566 +1-888-965-1860 ~19.73 miles west of Winter Haven
  • Includes a swimming pool
  • Affordable Highway hotel
From$84
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Vacation Club Mystic Dunes Orlando
+1-888-788-5576
7600 Mystic Dunes Lane, Kissimmee, FL 34747 +1-888-788-5576 ~22.07 miles north of Winter Haven
  • Pool in hotel: 4 Outdoor Pools 8AM-11PM
  • 4 star Golf Course hotel
From$48
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Suites Plant City An Ihg Hotel
+1-888-897-9207
2102 North Park Rd., Plant City, FL 33566 +1-888-897-9207 ~22.65 miles west of Winter Haven
  • Has swimming pool
  • 3-star Highway property
From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Westgate Town Center Resort
+1-888-311-4278
A7700 Westgate Blvd., Kissimmee, FL 34747 +1-888-311-4278 ~22.74 miles north of Winter Haven
  • Pool in hotel: 14 pools - all outdoor; open 8am to 10pm
  • Affordable Resort hotel
From$55
Very Good 4.0 /5 Read Reviews Call BookMore Details
Quality Inn Clermont West Kissimmee - Clermont
+1-888-469-4795
9330 West Us Highway 192, Clermont, FL 34714 +1-888-469-4795 ~22.80 miles north of Winter Haven
  • Pool details: Our outdoor pool is open from 10:00 AM to 10:00 PM. Our pool size is 22,024 gallons.
  • 2-star Highway property
From$57
Very Good 4.0 /5 Review Score Call BookMore Details
SureStay by Best Western Clermont Theme Park West - Clermont
+1-888-734-9421
9240 Us Highway 192, Clermont, FL 34714 +1-888-734-9421 ~22.81 miles north of Winter Haven
  • Pool available: Pool hours : 10 am to 10 pm. It is outdoor pool. And it is from 3 ft to 6 ft.
  • 3-star Highway property
From$49
Average 3.5 /5 Guest Reviews Call BookMore Details
Westgate Vacation Villas Resort
+1-888-841-5292
7700 Westgate Blvd., Kissimmee, FL 34747 +1-888-841-5292 ~22.83 miles north of Winter Haven
  • Pool available: 14 pools - all outdoor; open 8am to 10pm
  • Midscale Resort property
From$57
Very Good 4.0 /5 Review Score Call BookMore Details
Summer Bay Orlando by Exploria Resorts : 17805 Us Highway 192
+1-888-455-5160
17805 Us Highway 192, Clermont, FL 34714 +1-888-455-5160 ~22.86 miles north of Winter Haven
  • Pool in hotel: There are 6 outdoor Heated pools.
  • Three Star Resort hotel
From$44
Very Good 4.0 /5 Review Score Call BookMore Details
Orbit One Vacation Villas in Kissimmee
+1-888-965-8297
2950 Entry, Kissimmee, FL 34747 +1-888-965-8297 ~23.05 miles north of Winter Haven
  • Pool available: Outdoor Hot Tub(s) Outdoor Pool
  • 3-star Resort hotel
From$80
Very Good 4.0 /5 Read Reviews Call BookMore Details
Liki Tiki Village - Winter Garden
+1-888-906-6358
17777 Bali Blvd., Winter Garden, FL 34787 +1-888-906-6358 ~23.14 miles north of Winter Haven
  • Pool available: Liki Tiki has (3) pools Outdoor Pools 8AM-11PM
  • Affordable Resort property
From$38
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Ramada by Wyndham Kissimmee Gateway : 7470 West Irlo Bronson Memorial Highway
+1-888-749-6785
7470 West Irlo Bronson Memorial Highway, Kissimmee, FL 34747 +1-888-749-6785 ~23.20 miles north of Winter Haven
  • Has swimming pool: 8 am- 10 pm 2 Outdoor pools (1 heated)
  • Midscale Resort hotel
From$32
Average 3.0 /5 Latest Reviews Call BookMore Details
Travelodge by Wyndham Kissimmee / Orlando : 7475b West Irlo Bronson Memorial Highway
+1-888-878-9982
7475b West Irlo Bronson Memorial Highway, Kissimmee, FL 34747 +1-888-878-9982 ~23.32 miles north of Winter Haven
  • Includes a pool: Outdoor pool
  • Low priced property
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
Westgate Towers Resort - Kissimmee
+1-888-389-4485
7600 West Irlo Bronson Memorial Highway, Kissimmee, FL 34747 +1-888-389-4485 ~23.33 miles north of Winter Haven
  • Pool available: 3 heated outdoor pools, 3 spa tubs, 2 children pools; access to Westgate Town Center and Vacation Villas 14 pools and Waterpark(surcharge for waterpark applies).
  • Midscale Resort property
From$48
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Super 8 by Wyndham Kissimmee / Orlando : 7475 West Irlo Bronson Memorial Highway
+1-888-389-4121
7475 West Irlo Bronson Memorial Highway, Kissimmee, FL 34747 +1-888-389-4121 ~23.33 miles north of Winter Haven
  • Pool in hotel: Outdoor heated pool
  • Cheap Resort property
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
Galleria Palms Hotel in Kissimmee
+1-888-675-2083
3000 Maingate Lane, Kissimmee, FL 34747 +1-888-675-2083 ~23.34 miles north of Winter Haven
  • Pool in hotel: Outdoor heated pool with lounge chairs, tables and shade umbrellas. Pool towels are provided and pool is open daily from 8:00 AM to 11:00 PM.
  • Mid-scale Resort property
From$44
Very Good 4.0 /5 Read Reviews Call BookMore Details
Margaritaville Resort Orlando
+1-800-716-8490
8000 Fins Up Circle, Kissimmee, FL 34747 +1-800-716-8490 ~23.36 miles north of Winter Haven
  • Pool available: The hotel will offer Two Lagoon Style Pools with Soft Sand Beaches and One Resort Style Pool. Our Salty Rim Pool Bar is located by our Lagoon Style pools and will offer an inviting atmosphere for fun in the sun including cabanas, flat screen TV's, pool side games and much more.
  • Four-star Resort hotel
From$219
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Comfort Inn Kissimmee by Parks in Kissimmee
+1-800-805-5223
7675 West Irlo Bronson Memorial Highway, Kissimmee, FL 34747 +1-800-805-5223 ~23.42 miles north of Winter Haven
  • Pool details: Outdoor whirpool and Pool open from 9am-11pm
  • Affordable Downtown hotel
From$49
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Orlando Orange Lake Resort in Kissimmee
+1-888-965-1860
8505 West Irlo Bronson Memorial Highway, Kissimmee, FL 34747 +1-888-965-1860 ~23.46 miles north of Winter Haven
  • With a pool!
  • 4-star Resort hotel
From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Sonder Cirrus in Kissimmee
+1-888-788-5576
7888 West Irlo Bronson Memorial Highway, Kissimmee, FL 34747 +1-888-788-5576 ~23.46 miles north of Winter Haven
  • Has swimming pool: Outdoor pool open 8 am - 11 pm
  • Midscale Highway property
From$59
Average 3.0 /5 Review Score Call BookMore Details
Wyndham Orlando Resort & Conference Center Celebration Area : 3011 Maingate Ln
+1-888-897-9207
3011 Maingate Ln, Kissimmee, FL 34747 +1-888-897-9207 ~23.48 miles north of Winter Haven
  • Has swimming pool: 24 hours 2 Out-Door Heated Pools & Jacuzzi
  • Affordable Resort property
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Maingate Lakeside Resort - Kissimmee
+1-888-311-4278
7769 West Irlo Bronson Mem Highway, Kissimmee, FL 34747 +1-888-311-4278 ~23.57 miles north of Winter Haven
  • Pool available: 3 Pools Heated Seasonally
  • 3 star Resort property
The Grove Resort & Water Park Orlando - Winter Garden
+1-888-469-4795
14501 Grove Resort Ave., Winter Garden, FL 34787 +1-888-469-4795 ~23.96 miles north of Winter Haven
  • Pool in hotel: The Springs Pools - Three outdoor pools and oversized hot tub Poolside Cabanas and Lounge Chairs Surfari Water Park featuring a FlowRider Double surf simulator, dual water slides, a 695 foot lazy river, kids’ activities pool and zero-entry pool.
  • Mid-scale Resort hotel
From$250
Average 3.0 /5 Guest Reviews Call BookMore Details
Melia Orlando Celebration in Celebration
+1-888-734-9421
225 Celebration Pl, Celebration, FL 34747 +1-888-734-9421 ~24.42 miles northeast of Winter Haven
  • Pool in hotel: Open until 11pm. 360 degree infinity edge pool with zero entrance for small children. Outdoor, heated seasonally at 82 degrees. Poolside towel service, entertainment on weekends, food and beverage service provided.
  • 4 star Suburban property
From$99
Average 3.0 /5 Reviews Call BookMore Details
Delta Hotels by Marriott™ Orlando Celebration
+1-888-841-5292
2900 Pkwy. Blvd., Kissimmee, FL 34747 +1-888-841-5292 ~24.68 miles northeast of Winter Haven
  • Pool available: Pool Hours are 10am-10pm. We have two outdoor resort-style large pools. One of the pool has a 40 foot water slide. We also have two outdoor.
  • 3 star Resort hotel
From$49
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Parkway International Resort - Kissimmee
+1-888-455-5160
6200 Safari Trl, Kissimmee, FL 34747 +1-888-455-5160 ~24.84 miles northeast of Winter Haven
  • Pool in hotel: Pools are open from 8am till 10pm. We offer outdoor pools; children's, adults and hot tub.
  • Midscale Highway property
From$62
Very Good 4.0 /5 Reviews Call BookMore Details
Barefoot'n Resort in Kissimmee
+1-888-965-8297
2754 Florida Plaza Blvd., Kissimmee, FL 34746 +1-888-965-8297 ~24.91 miles northeast of Winter Haven
  • We have a pool
  • 3 star Suburban property
From$58
Very Good 4.0 /5 Reviews Call BookMore Details
Staybridge Suites – Orlando Royale Parc Suites : 5876 West Irlo Bronson Highway
+1-888-906-6358
5876 West Irlo Bronson Highway, Kissimmee, FL 34746 +1-888-906-6358 ~25.07 miles northeast of Winter Haven
  • Includes a pool: Pools hours from 9:00am to 11:00pm, Outdoor
  • 3 star Resort hotel
From$73
Very Good 4.5 /5 Reviews Call BookMore Details
Grand Hotel Kissimmee at Celebration in Kissimmee
+1-888-749-6785
3104 Pkwy. Blvd., Kissimmee, FL 34747 +1-888-749-6785 ~25.16 miles northeast of Winter Haven
  • Pool in hotel: The hotel has a large outdoor heated swimming pool that is open daily from 8:00 AM to 11:00 PM
  • Three Star Suburban property
From$55
Very Good 4.0 /5 Review Score Call BookMore Details
Seralago Hotel & Suites Main Gate East
+1-888-878-9982
5678 West Irlo Bronson Memorial Highway, Kissimmee, FL 34746 +1-888-878-9982 ~25.25 miles northeast of Winter Haven
  • Pool details: We have 2 Heated Outdoor Olympic Sized Swimming Pools with Jacuzzis. Also 1 heated kiddie pool. Pools open from 8am - 11pm.
  • Midscale Resort property
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
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