Holiday rentals with a pool in Gainesville

Luxurious three-bedroom condo at Celebration Point

This well-appointed condo offers the perfect home base for your Gainesville visit—just minutes from the UF, Shands, and the city’s best shopping and dining. Ideal for families or groups, the spacious layout features three bedrooms, each with its own private bath, ensuring comfort and convenience. Nestled in a quiet, gated community, you’ll enjoy access to a recreation complex complete with: swimming pool & hot tub, fitness room, tennis and basketball courts. Plus, just ¾ mile from I-75 Exit 384.

Condo in the Heart of Haile Village-Great Location

Stay in the heart of award-winning Haile Village, located within the community of Haile Plantation. Condo balcony overlooks a popular tranquil park. Enjoy relaxing sounds from the large fountain and twinkling lights at night. Walk to restaurants, coffee & dessert shop, plus wine & gift shopping. Condo is the perfect location for Village Hall weddings & events! Saturday morning Farmers Market, spa and kids play space are just feet away! Enjoy Haile's nature trails, Turtle Pond and nature views.

Gated Golf Getaway close to Springs and UF

A clean and comfortable home, situated in a gated community with a public 18 hole golf course and practice range, reasonably priced restaurant, swimming pool (seasonally, quick walk or drive), playground, and tennis courts available to guests. The home features a screened patio with table, chairs and gas grill. There are 3 bedrooms each with a queen bed. Located on U.S. highway 441 just 20 minutes from U.F. sports stadiums and Hospitals. Convenient shopping and restaurants 10 minutes by car.

Tiny Farmhouse on The Grove

Take it easy at this unique and peaceful getaway just minutes outside the city of Alachua and 20 minutes from Gainesville. A tiny house on the farm surrounded by nature, wildlife, and farm animals. We have 2 goats, 2 zebus, and 4 donkeys that make up our little farmhouse retreat. The cabin is stylish and cozy offering a full size bed, futon, WiFi and TV. . Has everything you need for a relaxing getaway. 7 min to Alachua 17 min to High Springs 15 min to Gainesville 28 min to Ginnie Springs

4 Bedrooms, Private Pool + HOT TUB

Hi I'm John with Gainesville STR. Check out our great ratings and reviews! Just a 10 minute drive to O'Connell Center for graduate/white coat ceremonies. Pool heating is available for extra fee. Message us for details. Your family home in Gainesville awaits - Close to the stadium and Shands with an 800 sq ft HEATED pool , hot tub, BBQ grill and XBOX Live. Ben Hill Griffin Stadium / O'Connell Center - 10 minutes Shands Medical Center - 12 minutes Ginnie Springs - 45 minutes

Short walk to Shands, VA, University of Florida 1

Comfortable condo located one block from Shands Hospital, VA Hospital, two blocks to the University of Florida Campus, and 1.5 miles to the football stadium (30 minute walk). The ground level condo is a two bedroom/1 bathroom. Each bedroom has a walk in closet, queen bed, chest of drawers. The kitchen is fully furnished with dishwasher, gas stove, microwave, and dishes. High Speed internet and cable are included. Sleeps 4 comfortably- No Dogs are allowed in the complex.

The YinYang | King Bed • Workspace • Full Kitchen

Fully renovated Zen condo perfect for your visit to Gainesville. Located a stone's throw from I-75, North Florida Regional Medical Center, and not far from UF and Shands, this updated cozy yet modern apartment has everything you need for a pleasant stay. Fully equipped with a KING bed, pullout sofa, and dedicated workplace. Enjoy your morning coffee or evening drink in the outdoor patio. Whether you're traveling for work or leisure, this apartment has it all.

Modern Muse w/Firepit & Heated Pool Option

Enjoy a Luxury stay for your next getaway. This MODERN PARADISE provides you everything and more. All lighting, TV’s and Living Area surround sound (Sonos) are Alexa controlled allowing you to sit and relax while Alexa does the work. Wonderful amenities range from heated toilet seat bidets, 4 system shower panels with rain shower, a Heated Pool Add-On Option and Cabannas, 72in Fireglass Firepit, Gym Area w/TV for Streaming Workouts, Beverage Bar and more

Cozy Retreat 2BR Escape Near Celebration Pointe

Stay in this stylish, renovated Gainesville condo with a private one-car garage and reserved parking. Centrally located, you’re steps from restaurants, coffee shops, dessert spots, shopping, and a movie theater. Perfect for UF events, Gators football, graduations, or visits to Shands/UF Health, this modern, comfortable retreat offers everything you need for a relaxing, hassle-free stay with easy access to Midtown Gainesville and downtown attractions.

Sanctuary at Oaks | Full Kitchen • Near I75

↞----- Designer Sanctuary | Fully-Renovated Condo -----↠ ▻ Right off I-75 & 3 miles to University of Florida ▻ 2 bedrooms & 2.5 baths ▻ 5 beds for up to 8 guests ▻ Bright and Spacious ▻ Thoughtful, concept design This is the perfect spot to access everything the Gainesville area offers; it's near shopping, eating, natural springs, and down the road from UF. Perfect for couples, families, or friends who want all the amenities with a touch of luxury.

Orange Blossom Retreat | Pool, Hot Tub, and Game's

Welcome to the Orange Blossom Retreat! This home has an above ground pool surrounded by a deck, a hot tub under a wooden gazebo, and a climate controlled garage with a game room! The living room features a large couch facing the 75inch Tv and sound bar. The master bed has a nectar king mattress with a Tv for late night television. Orange Blossom Retreat is centrally located in Gainesville making it an easy commute to any side of town.

Great Location! Walk to Shands/UF/VA/Vet

This condo is just a short walk away from Shands Hospital, University of Florida, the Veterinary School, and the VA Hospital. A 5 minute drive to downtown. It's a one-bedroom condo on the first floor. Whether you're in town visiting Gainesville, at the University of Florida for an event, or on a clinical rotation, this place is in a great location. Within walking distance to football and basketball games.